coproporphyrin i profile

Coproporphyrin I is a type of porphyrin, a class of organic compounds that play a crucial role in various biological processes, particularly in the biosynthesis of heme. It is an abnormal isomer of coproporphyrin, a natural product found in urine. Coproporphyrin I is characterized by its unique structural arrangement of its four carboxyl groups, which differ from the normal isomer coproporphyrin III. This structural difference results in coproporphyrin I being unable to bind to the iron atom necessary for heme formation. It is therefore considered a protoporphyrin precursor. Coproporphyrin I accumulation is associated with certain genetic disorders, such as congenital erythropoietic porphyria (CEP), leading to various clinical manifestations. It is also associated with various environmental exposures, including exposure to heavy metals and certain medications. The study of coproporphyrin I is vital for understanding porphyrin metabolism, diagnosing porphyria, and exploring potential therapeutic interventions. It is also valuable for developing methods to detect and monitor environmental contamination with porphyrin precursors.'

coproporphyrin I: RN given refers to cpd with specified locants; see also record for coproporphyrin III; zinc coproporphyrin I is fluorescent and a characteristic component of meconium [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	68271
CHEBI ID	28421
SCHEMBL ID	578775
SCHEMBL ID	578776
MeSH ID	M0098849

Synonym
nsc-267073
21h,7,12,17-tetrapropanoic acid, 3,8,13,18-tetramethyl
2,12,17-porphinetetrapropionic acid, 3,8,13,18-tetramethyl-
nsc267073
21h,7,12,17-tetrapropanoic acid, 3,8,13,18-tetramethyl- (va
CHEBI:28421
3-[(4z,10z,15z,19z)-7,12,17-tris-(2-carboxy-ethyl)-3,8,13,18-tetramethyl-22,24-dihydro-porphin-2-yl]-propionic acid
3-[(1z,4z,9z,15z)-7,12,17-tris(2-carboxyethyl)-3,8,13,18-tetramethyl-21,23-dihydroporphyrin-2-yl]propanoic acid
coproporphyrin i
C05769 ,
531-14-6
3-[7,12,17-tris(2-carboxyethyl)-3,8,13,18-tetramethyl-21,22-dihydroporphyrin-2-yl]propanoic acid
FT-0665165
21h,23h-porphine-2,7,12,17-tetrapropanoic acid, 3,8,13,18-tetramethyl- (van)
einecs 208-502-3
21h,23h-porphine-2,7,12,17-tetrapropanoic acid, 3,8,13,18-tetramethyl-
nsc 267073
2,7,12,17-porphinetetrapropionic acid, 3,8,13,18-tetramethyl- (van)
3,8,13,18-tetramethyl-21h,23h-porphine-2,7,12,17-tetrapropionic acid
SCHEMBL578775
SCHEMBL578776
VORBHEGMEBOMMB-JRHDEHKPSA-N
koproporphyrin i
3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1{3,6}.1{8,11}.1{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid
2,7,12,17-porphinetetrapropionic acid, 3,8,13,18-tetramethyl-
3,8,13,18-tetramethyl-21h,23h-porphine-2,7,12,17-tetrapropanoic acid
BW4SWA9YWC
Q26841013
Q27103688
coproporphyrin i, 85per cent(contain 13per cent coproporphyrin lll)
DTXSID90883425

Excerpt	Reference	Relevance
"Coproporphyrin I (CPI) is an endogenous biomarker of organic anion transporting polypeptide 1B transporter (OATP1B). "	( Coproporphyrin I as an Endogenous Biomarker to Detect Reduced OATP1B Activity and Shift in Elimination Route in Chronic Kidney Disease. Chu, X; Galetin, A; Ogungbenro, K; Scotcher, D; Takita, H; Yee, KL, 2022)	3.61
"Coproporphyrin I (CP-I) is an endogenous biomarker supporting the prediction of drug-drug interactions (DDIs) involving hepatic organic anion transporting polypeptide 1B (OATP1B). "	( Cluster Gauss-Newton method analyses of PBPK model parameter combinations of coproporphyrin-I based on OATP1B-mediated rifampicin interaction studies. Aoki, Y; Chiba, K; Kusuhara, H; Mochizuki, T; Rodrigues, AD; Sugiyama, Y; Yoshikado, T, 2022)	2.16
"Coproporphyrin I (CPI) is an endogenous biomarker of OATP1B activity and associated drug-drug interactions. "	( PBPK Model of Coproporphyrin I: Evaluation of the Impact of SLCO1B1 Genotype, Ethnicity, and Sex on its Inter-Individual Variability. Barnett, S; Galetin, A; Ménochet, K; Ogungbenro, K; Shen, H; Takita, H; Zhang, Y, 2021)	2.42
"Zinc coproporphyrin I (ZnCP-I) is a photosensitive molecule and a major component of meconium. "	( Zinc coproporphyrin I derived from meconium has an antitumor effect associated with singlet oxygen generation. Asahina, T; Hirano, T; Horiuchi, K; Kanayama, N; Kohmura, Y; Kohno, E; Murakami, H; Ooi, H; Ozawa, H; Sugihara, K; Tamura, N; Yaguchi, C, 2013)	1.42

Excerpt	Reference	Relevance
" Population pharmacokinetic analysis was conducted to assess whether MTX clearance (MTXCL) was associated with the basal UCP I/(I + III) ratio, its variation during MTX infusion, the DIS or other common covariates."	( Urinary coproporphyrin I/(I + III) ratio as a surrogate for MRP2 or other transporter activities involved in methotrexate clearance. Benz-de Bretagne, I; Choquet, S; Gyan, E; Hoang-Xuan, K; Houillier, C; Hulot, JS; Le Gouge, A; Le Guellec, C; Lissandre, S; Zahr, N, 2014)	0.84
" We previously constructed a physiologically-based pharmacokinetic (PBPK) model of rifampicin accounting for the components for the induction of cytochrome P450 (CYP) 3A/CYP2C9 and the inhibition of organic anion transporting polypeptide 1B (OATP1B)."	( Expanded Physiologically-Based Pharmacokinetic Model of Rifampicin for Predicting Interactions With Drugs and an Endogenous Biomarker via Complex Mechanisms Including Organic Anion Transporting Polypeptide 1B Induction. Asaumi, R; Imawaka, H; Kusuhara, H; Lee, W; Menzel, K; Nunoya, KI; Sugiyama, Y, 2019)	0.51
"Despite a recent expansion in the recognition of the potential utility of coproporphyrin (CP) as an endogenous biomarker of organic anion-transporting polypeptide (OATP) 1B activity, there have been few detailed studies of CP's pharmacokinetic behavior and an overall poor understanding of its pharmacokinetic fate from tissues and excretion."	( Absorption and Disposition of Coproporphyrin I (CPI) in Cynomolgus Monkeys and Mice: Pharmacokinetic Evidence to Support the Use of CPI to Inform the Potential for Organic Anion-Transporting Polypeptide Inhibition. Fancher, RM; Gan, J; Gu, X; Hong, Y; Lai, Y; Shen, H; Sinz, M; Tian, Y; Wang, L, 2020)	0.85

Excerpt	Reference	Relevance
" Collectively, we conclude that CP-I and CP-III in plasma and urine can be appropriate endogenous biomarkers specifically and reliably reflecting OATP inhibition, and thus the measurement of these molecules can serve as a useful tool to assess OATP drug-drug interaction liabilities in early clinical studies."	( Coproporphyrins in Plasma and Urine Can Be Appropriate Clinical Biomarkers to Recapitulate Drug-Drug Interactions Mediated by Organic Anion Transporting Polypeptide Inhibition. Cheng, Y; Dai, J; Date, O; Gaud, N; Holenarsipur, VK; Humphreys, WG; Lai, Y; Langish, R; Mandlekar, S; Marathe, P; Murugesan, S; Rajanna, P; Selvam, S; Shen, H; Shipkova, P, 2016)	0.43
" These data demonstrate the potential of CP-I and CP-III as endogenous biomarkers to predict the drug-drug interaction (DDI) related to hepatic OATP1B inhibition."	( Development of an LC-MS method to quantify coproporphyrin I and III as endogenous biomarkers for drug transporter-mediated drug-drug interactions. Diels, L; Dillen, L; Kunze, A; Njumbe Ediage, E; Snoeys, J; Verhaeghe, T; Vroman, A, 2018)	0.74
"This study evaluated coproporphyrin I (CPI) as a selective endogenous biomarker of OATP1B-mediated drug-drug interactions (DDIs) relative to clinical probe rosuvastatin using nonlinear mixed-effect modeling."	( Gaining Mechanistic Insight Into Coproporphyrin I as Endogenous Biomarker for OATP1B-Mediated Drug-Drug Interactions Using Population Pharmacokinetic Modeling and Simulation. Barnett, S; Galetin, A; Humphreys, WG; Lai, Y; Ménochet, K; Ogungbenro, K; Shen, H, 2018)	1.08
"Coproporphyrin (CP) I and III have recently been proposed as endogenous clinical biomarkers to predict organic anion-transporting polypeptide 1B (OATP1B)-mediated drug-drug interactions (DDIs)."	( Clinical Investigation of Coproporphyrins as Sensitive Biomarkers to Predict Mild to Strong OATP1B-Mediated Drug-Drug Interactions. Dillen, L; Ediage, EN; Kunze, A; Monshouwer, M; Snoeys, J, 2018)	0.48
" Furthermore, CPI and CPIII plasma concentrations were determined from participants of three independent clinical trials who were administered with either a strong, moderate, or mild clinical OATP1B inhibitor."	( Clinical Investigation of Coproporphyrins as Sensitive Biomarkers to Predict Mild to Strong OATP1B-Mediated Drug-Drug Interactions. Dillen, L; Ediage, EN; Kunze, A; Monshouwer, M; Snoeys, J, 2018)	0.48
"A robust UHPLC-MS/MS assay was developed and validated for CP-I and CP-III in plasma, and is currently applied to clinical studies to confirm suitability of Coproporphyrins as a potential substitute for drug-drug interaction study."	( UHPLC-MS/MS bioanalysis of human plasma coproporphyrins as potential biomarkers for organic anion-transporting polypeptide-mediated drug interactions. Burrrell, R; Easter, J; Kadiyala, P; Kandoussi, H; Lai, Y; Langish, R; Marathe, P; Mariannino, T; Paterson, P; Pillutla, R; Santockyte, R; Shah, K; Shen, H; Shipkova, P; Zeng, J; Zhang, Y, 2018)	0.48
"Evaluation of the organic anion transporting polypeptide (OATP) 1B-mediated drug-drug interaction (DDI) potential is important for drug development."	( Quantitative prediction of OATP1B-mediated drug-drug interactions using endogenous biomarker coproporphyrin I. Bessho, K; Shigemi, R; Takubo, H; Watari, R, 2022)	0.94

Excerpt	Relevance	Reference
" Significant dose-response relationship was observed between control and treatment groups after 1, 4, 24, 32, 48, 56, 88, 96 and 104 weeks."	( Urinary arsenic and porphyrin profile in C57BL/6J mice chronically exposed to monomethylarsonous acid (MMAIII) for two years. Krishnamohan, M; Lam, PK; Moore, MR; Ng, JC; Qi, L, 2007)	0.34
" Moreover, CP-I and CP-III plasma levels in human subjects dosed with a clinically confirmed OATP inhibitor were significantly increased compared to their baseline levels."	( Development of an LC-MS method to quantify coproporphyrin I and III as endogenous biomarkers for drug transporter-mediated drug-drug interactions. Diels, L; Dillen, L; Kunze, A; Njumbe Ediage, E; Snoeys, J; Verhaeghe, T; Vroman, A, 2018)	0.74
" The established PBPK model was capable of accurately predicting complex rifampicin-induced alterations in the profiles of glibenclamide, repaglinide, and coproporphyrin I (an endogenous biomarker of OATP1B activities) with various dosing regimens."	( Expanded Physiologically-Based Pharmacokinetic Model of Rifampicin for Predicting Interactions With Drugs and an Endogenous Biomarker via Complex Mechanisms Including Organic Anion Transporting Polypeptide 1B Induction. Asaumi, R; Imawaka, H; Kusuhara, H; Lee, W; Menzel, K; Nunoya, KI; Sugiyama, Y, 2019)	0.71
" Coproporphyrin-I (CP-I) is a sensitive and specific endogenous probe for phenotyping OATP1B activity and a potentially useful tool to individualize the dosage of OATP1B substrates."	( Simultaneous quantification of coproporphyrin-I and 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid in human plasma using ultra-high performance liquid chromatography coupled to tandem mass spectrometry. Ando, T; Itoh, H; Mimata, H; Ohno, K; Ono, H; Sasamoto, Y; Shin, T; Suzuki, Y; Tanaka, R; Yoshijima, C, 2020)	0.56

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	16 (17.78)	18.7374
1990's	17 (18.89)	18.2507
2000's	12 (13.33)	29.6817
2010's	28 (31.11)	24.3611
2020's	17 (18.89)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	8 (8.51%)	5.53%
Reviews	2 (2.13%)	6.00%
Case Studies	7 (7.45%)	4.05%
Observational	1 (1.06%)	0.25%
Other	76 (80.85%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	9.29	4	1	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	1.96	1	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
carbamates [no description available]	2.21	1	0	amino-acid anion
glycine [no description available]	1.97	1	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
porphobilinogen [no description available]	2.67	3	0	aralkylamino compound; dicarboxylic acid; pyrroles	Escherichia coli metabolite; metabolite; mouse metabolite
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	2.25	1	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.21	1	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	1.99	1	0	carboxamidine; guanidines; one-carbon compound
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	7.25	1	0	benzoic acids; sulfonamide	uricosuric drug
protoporphyrin ix protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.	3.51	8	0
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.03	1	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	7	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	1.98	1	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	3.7	1	1	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
benzoyl peroxide Benzoyl Peroxide: A peroxide derivative that has been used topically for BURNS and as a dermatologic agent in the treatment of ACNE and POISON IVY DERMATITIS. It is used also as a bleach in the food industry.	2.03	1	0	carbonyl compound
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	1.96	1	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.41	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	3.98	2	1	indazole
hexadecanedioic acid hexadecanedioic acid : An alpha,omega-dicarboxylic acid that is the 1,14-dicarboxy derivative of tetradecane.	2.15	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite
dehydroepiandrosterone sulfate Dehydroepiandrosterone Sulfate: The circulating form of a major C19 steroid produced primarily by the ADRENAL CORTEX. DHEA sulfate serves as a precursor for TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE.. dehydroepiandrosterone sulfate : A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.	2.15	1	0	17-oxo steroid; steroid sulfate	EC 2.7.1.33 (pantothenate kinase) inhibitor; human metabolite; mouse metabolite
arsenic trioxide Arsenic Trioxide: An inorganic compound with the chemical formula As2O3 that is used for the treatment of ACUTE PROMYELOCYTIC LEUKEMIA in patients who have relapsed from, or are resistant to, conventional drug therapy.	1.98	1	0
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2	1	0
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.41	2	0	benzenes; phenyl acetates
pravastatin Pravastatin: An antilipemic fungal metabolite isolated from cultures of Nocardia autotrophica. It acts as a competitive inhibitor of HMG CoA reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES).. pravastatin : A carboxylic ester resulting from the formal condensation of (S)-2-methylbutyric acid with the hydroxy group adjacent to the ring junction of (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid. Derived from microbial transformation of mevastatin, pravastatin is a reversible inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA). The sodium salt is used for lowering cholesterol and preventing cardiovascular disease. It is one of the lower potency statins, but has the advantage of fewer side effects compared with lovastatin and simvastatin.	8.98	2	1	3-hydroxy carboxylic acid; carbobicyclic compound; carboxylic ester; hydroxy monocarboxylic acid; secondary alcohol; statin (semi-synthetic)	anticholesteremic drug; environmental contaminant; metabolite; xenobiotic
atorvastatin [no description available]	2.17	1	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
repaglinide [no description available]	2.21	1	0	piperidines
mesoporphyrin ix mesoporphyrin IX: RN given refers to parent cpd; mesoheme is the iron salt of mesoporphyrin IX. mesoporphyrin IX : A member of the class of mesoporphyrins obtained by formal hydrogenation of the two vinyl groups in protoporphyrin.	1.96	1	0
uroporphyrin iii [no description available]	2.42	2	0
uroporphyrin i uroporphyrin I: RN given refers to parent cpd	3.1	5	0
coumarin 153 coumarin 153: structure in first source	2.15	1	0	7-aminocoumarins	fluorochrome
cholest-5-ene-3,4-diol cholest-5-ene-3,4-diol: RN given refers to (3beta,4beta)-isomer	2.25	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.03	1	0	cobalt group element atom; metal allergen	micronutrient
zinc coproporphyrin iii coproporphyrin III: RN given refers to unlabeled parent cpd; see also record for coproporphyrin I	11.4	44	6
nitisinone [no description available]	2	1	0	(trifluoromethyl)benzenes; C-nitro compound; cyclohexanones; mesotrione	EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor
3-carboxy-4-methyl-5-propyl-2-furanpropionic acid 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid: structure in first source. 2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid : A furoic acid that is furan-3-carboxylic acid substituted by a methyl group at position 4, a propyl group at position 5 and a 2-carboxyethyl group at position 2. It is a potent uremic toxin that has been found to accumulate in human serum of patients with chronic kidney diseases.	2.69	2	0	dicarboxylic acid; furoic acid	human metabolite; uremic toxin
methotrexate [no description available]	9.4	1	1	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	7.08	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
methanearsonous acid methanearsonous acid: RN given refers to parent cpd. methylarsonous acid : A one-carbon compound that is arsonous acid in which the hydrogen attached to arsenic is replaced by a methyl group.	2.03	1	0	arsonous acids; one-carbon compound	carcinogenic agent; human xenobiotic metabolite; poison
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	2	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
4-maleimido-2,2,6,6-tetramethylpiperidinooxyl 4-maleimido-TEMPO : A member of the class of piperidines that is TEMPO carrying a maleimido group at position 4.	1.99	1	0	aminoxyls; dicarboximide; maleimides; piperidines	radical scavenger; spin label
zinc protoporphyrin ix [no description available]	2.06	1	0
bilirubin [no description available]	2.92	4	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
isotretinoin Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.	2.03	1	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
pitavastatin pitavastatin : A dihydroxy monocarboxylic acid that is (6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]hept-6-enoic acid in which the two hydroxy groups are located at positions 3 and 5 (the 3R,5S-stereoisomer). Used as its calcium salt for treatment of hypercholesterolemia (elevated levels of cholesterol in the blood) on patients unable to sufficiently lower their cholesterol levels by diet and exercise.	2.17	1	0	cyclopropanes; dihydroxy monocarboxylic acid; monofluorobenzenes; quinolines; statin (synthetic)	antioxidant
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.65	3	0	carbon group element atom; elemental lead; metal atom	neurotoxin
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	2.91	4	0	metalloid atom; pnictogen	micronutrient
piperidines Piperidines: A family of hexahydropyridines.	2.21	1	0
letermovir letermovir: has antiviral activity; structure in first source	2.41	1	0
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.94	4	0
minocycline Minocycline: A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.. minocycline : A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.	2.03	1	0
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.15	1	0	benzenes; hydroxycoumarin; methyl ketone
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	5.18	3	1
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	6.99	14	1	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor

Condition	Relationship Strength	Studies	Trials
Chronic Kidney Diseases [description not available]	2.72	2	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.72	2	0
Fatty Liver, Nonalcoholic [description not available]	2.31	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.31	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.73	3	0
Rheumatoid Arthritis [description not available]	2.31	1	0
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.31	1	0
Adenocarcinoma, Basal Cell [description not available]	2.17	1	0
Colorectal Cancer [description not available]	2.17	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.17	1	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.17	1	0
Chronic Kidney Failure [description not available]	2.21	1	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	2.21	1	0
Breast Cancer [description not available]	3.59	1	1
Breast Neoplasms Tumors or cancer of the human BREAST.	3.59	1	1
Germinoblastoma [description not available]	4.4	1	1
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	4.4	1	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.13	1	0
Aneurysm, Anterior Cerebral Artery [description not available]	2.05	1	0
Hemorrhage, Subarachnoid [description not available]	2.05	1	0
Acute Porphyria [description not available]	3.81	2	1
Intracranial Aneurysm Abnormal outpouching in the wall of intracranial blood vessels. Most common are the saccular (berry) aneurysms located at branch points in CIRCLE OF WILLIS at the base of the brain. Vessel rupture results in SUBARACHNOID HEMORRHAGE or INTRACRANIAL HEMORRHAGES. Giant aneurysms (	2.05	1	0
Subarachnoid Hemorrhage Bleeding into the intracranial or spinal SUBARACHNOID SPACE, most resulting from INTRACRANIAL ANEURYSM rupture. It can occur after traumatic injuries (SUBARACHNOID HEMORRHAGE, TRAUMATIC). Clinical features include HEADACHE; NAUSEA; VOMITING, nuchal rigidity, variable neurological deficits and reduced mental status.	2.05	1	0
Porphyria, Acute Intermittent An autosomal dominant porphyria that is due to a deficiency of HYDROXYMETHYLBILANE SYNTHASE in the LIVER, the third enzyme in the 8-enzyme biosynthetic pathway of HEME. Clinical features are recurrent and life-threatening neurologic disturbances, ABDOMINAL PAIN, and elevated level of AMINOLEVULINIC ACID and PORPHOBILINOGEN in the urine.	3.81	2	1
Amnionitis [description not available]	2.07	1	0
Aspiration, Meconium [description not available]	3.81	2	1
Amniotic Fluid Embolism [description not available]	7.72	3	0
Chorioamnionitis INFLAMMATION of the placental membranes (CHORION; AMNION) and connected tissues such as fetal BLOOD VESSELS and UMBILICAL CORD. It is often associated with intrauterine ascending infections during PREGNANCY.	2.07	1	0
Meconium Aspiration Syndrome A condition caused by inhalation of MECONIUM into the LUNG of FETUS or NEWBORN, usually due to vigorous respiratory movements during difficult PARTURITION or respiratory system abnormalities. Meconium aspirate may block small airways leading to difficulties in PULMONARY GAS EXCHANGE and ASPIRATION PNEUMONIA.	3.81	2	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.72	3	0
Erythrohepatic Protoporphyria [description not available]	2.07	1	0
Actinic Reticuloid Syndrome [description not available]	2.07	1	0
Protoporphyria, Erythropoietic An autosomal dominant porphyria that is due to a deficiency of FERROCHELATASE (heme synthetase) in both the LIVER and the BONE MARROW, the last enzyme in the 8-enzyme biosynthetic pathway of HEME. Clinical features include mainly neurological symptoms, rarely cutaneous lesions, and elevated levels of protoporphyrin and COPROPORPHYRINS in the feces.	2.07	1	0
Asystole [description not available]	2.08	1	0
Edema, Pulmonary [description not available]	2.08	1	0
Heart Arrest Cessation of heart beat or MYOCARDIAL CONTRACTION. If it is treated within a few minutes, heart arrest can be reversed in most cases to normal cardiac rhythm and effective circulation.	2.08	1	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	2.08	1	0
Benign Neoplasms [description not available]	2.08	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.08	1	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.08	1	0
Porphyria [description not available]	4.62	6	0
Porphyrias A diverse group of metabolic diseases characterized by errors in the biosynthetic pathway of HEME in the LIVER, the BONE MARROW, or both. They are classified by the deficiency of specific enzymes, the tissue site of enzyme defect, or the clinical features that include neurological (acute) or cutaneous (skin lesions). Porphyrias can be hereditary or acquired as a result of toxicity to the hepatic or erythropoietic marrow tissues.	4.62	6	0
Remission, Spontaneous A spontaneous diminution or abatement of a disease over time, without formal treatment.	2.01	1	0
Porphyria Cutanea Tarda An autosomal dominant or acquired porphyria due to a deficiency of UROPORPHYRINOGEN DECARBOXYLASE in the LIVER. It is characterized by photosensitivity and cutaneous lesions with little or no neurologic symptoms. Type I is the acquired form and is strongly associated with liver diseases and hepatic toxicities caused by alcohol or estrogenic steroids. Type II is the familial form.	7.4	2	0
Poisoning, Lead [description not available]	4.02	3	1
Lead Poisoning Poisoning that results from chronic or acute ingestion, injection, inhalation, or skin absorption of LEAD or lead compounds.	4.02	3	1
Retinal Pigment Epithelial Detachment [description not available]	1.93	1	0
Retinal Detachment Separation of the inner layers of the retina (neural retina) from the pigment epithelium. Retinal detachment occurs more commonly in men than in women, in eyes with degenerative myopia, in aging and in aphakia. It may occur after an uncomplicated cataract extraction, but it is seen more often if vitreous humor has been lost during surgery. (Dorland, 27th ed; Newell, Ophthalmology: Principles and Concepts, 7th ed, p310-12).	1.93	1	0
Acne [description not available]	2.03	1	0
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	2.03	1	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.03	1	0
Hyperbilirubinemia, Hereditary Inborn errors of bilirubin metabolism resulting in excessive amounts of bilirubin in the circulating blood, either because of increased bilirubin production or because of delayed clearance of bilirubin from the blood.	2.66	3	0
Liver Dysfunction [description not available]	3.3	2	0
Biliary Tract Diseases Diseases in any part of the BILIARY TRACT including the BILE DUCTS and the GALLBLADDER.	2.9	1	0
Liver Diseases Pathological processes of the LIVER.	3.3	2	0
Arsenic Encephalopathy [description not available]	1.98	1	0
Dubin-Johnson Syndrome [description not available]	3.08	5	0
Diseases in Twins Disorders affecting TWINS, one or both, at any age.	1.99	1	0
Symptom Cluster [description not available]	2.67	3	0
Syndrome A characteristic symptom complex.	2.67	3	0
Genetic Diseases [description not available]	2	1	0
Amino Acid Metabolism Disorders, Inborn [description not available]	2	1	0
Genetic Diseases, Inborn Diseases that are caused by genetic mutations present during embryo or fetal development, although they may be observed later in life. The mutations may be inherited from a parent's genome or they may be acquired in utero.	2	1	0
Constitutional Liver Dysfunction [description not available]	1.97	1	0
Alcohol Abuse [description not available]	1.97	1	0
Bile Duct Obstruction, Intrahepatic [description not available]	1.97	1	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	1.97	1	0
Cholestasis, Intrahepatic Impairment of bile flow due to injury to the HEPATOCYTES; BILE CANALICULI; or the intrahepatic bile ducts (BILE DUCTS, INTRAHEPATIC).	1.97	1	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	1.97	1	0
Dermatoses [description not available]	1.96	1	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	1.96	1	0
Icterus [description not available]	1.96	1	0
Jaundice A clinical manifestation of HYPERBILIRUBINEMIA, characterized by the yellowish staining of the SKIN; MUCOUS MEMBRANE; and SCLERA. Clinical jaundice usually is a sign of LIVER dysfunction.	1.96	1	0

coproporphyrin i

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Research Demand Index: 30.91

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