Compounds > 1-0-octadecyl 2-0-acetyl sn-glycero-3-phosphorylcholine
Page last updated: 2024-12-04

1-0-octadecyl 2-0-acetyl sn-glycero-3-phosphorylcholine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1-O-octadecyl 2-O-acetyl sn-glycero-3-phosphorylcholine, also known as **18:0,2-acetyl-GPC**, is a synthetic analog of **platelet-activating factor (PAF)**.

Here's a breakdown:

* **Platelet-activating factor (PAF)** is a potent bioactive phospholipid that plays a critical role in various biological processes, including inflammation, immune responses, and blood coagulation.
* **18:0,2-acetyl-GPC** is structurally similar to PAF but differs in the fatty acyl chain at the sn-1 position. It is specifically designed to be a **selective agonist** for PAF receptors.

**Why is it important for research?**

18:0,2-acetyl-GPC serves as a valuable tool for researchers studying PAF and its role in various biological processes. Here's why:

* **Selective Agonist:** Unlike PAF, which can activate multiple receptors, 18:0,2-acetyl-GPC specifically targets PAF receptors. This selectivity allows researchers to study the specific effects of PAF signaling without interference from other pathways.
* **Understanding PAF Signaling:** By using 18:0,2-acetyl-GPC, researchers can investigate the downstream signaling pathways activated by PAF receptors. This knowledge helps in understanding the molecular mechanisms underlying PAF's diverse biological effects.
* **Drug Discovery:** 18:0,2-acetyl-GPC and other PAF analogs are being investigated as potential therapeutic agents for conditions like asthma, sepsis, and stroke. They can either block PAF signaling (antagonists) or mimic its actions (agonists) depending on the desired therapeutic effect.

**In summary, 18:0,2-acetyl-GPC is a valuable research tool because it provides a selective and controllable way to study PAF signaling, contributing to our understanding of PAF's role in health and disease, and informing the development of novel PAF-modulating drugs.**

You're asking about **1-O-octadecyl 2-O-acetyl sn-glycero-3-phosphorylcholine**, often abbreviated as **18:0-2Ac-GPC**. Let's break down what it is and its importance in research:

**What it is:**

* **Structure:** It's a **phospholipid**, a type of fat-like molecule that is a major component of cell membranes.
* **1-O-octadecyl:** This means a saturated fatty acid chain with 18 carbon atoms (octadecyl) is attached to the first carbon of the glycerol backbone.
* **2-O-acetyl:** An acetyl group (CH3CO-) is attached to the second carbon of the glycerol backbone.
* **sn-glycero-3-phosphorylcholine:** This denotes the glycerol backbone, a phosphate group, and a choline head group (a nitrogenous compound).

* **Function:** 18:0-2Ac-GPC is not a naturally occurring phospholipid. It's a synthetic compound that mimics the structure of naturally occurring phosphatidylcholines (PCs) found in cell membranes.

**Why it's important in research:**

* **Cell Membrane Studies:**
* 18:0-2Ac-GPC is a useful tool for studying **membrane fluidity and dynamics**. The acetyl group alters the physical properties of the molecule, making it more fluid and easier to penetrate cell membranes. This makes it helpful for understanding how membranes function and how drugs interact with them.
* **Drug Delivery:**
* 18:0-2Ac-GPC has potential applications in **drug delivery systems**. Its modified structure allows it to act as a carrier molecule that can encapsulate and deliver drugs across cell membranes. This could be particularly beneficial for delivering drugs that have difficulty crossing cell membranes on their own.
* **Neuroprotection:**
* Some research suggests that 18:0-2Ac-GPC may have **neuroprotective properties**. It has been shown to improve cognitive function and protect against neuronal damage in animal models. This suggests potential therapeutic applications in treating neurological disorders.
* **Cancer Research:**
* 18:0-2Ac-GPC is being investigated for its potential role in **cancer treatment**. Some studies suggest that it may be able to inhibit tumor growth and even induce apoptosis (programmed cell death) in cancer cells.

**Overall, 18:0-2Ac-GPC is a valuable tool in research due to its unique structural properties and potential applications in various fields, including cell membrane biology, drug delivery, neuroprotection, and cancer research.**

**Important Note:** It's crucial to remember that research on 18:0-2Ac-GPC is still ongoing, and its clinical applications are yet to be fully established.

2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has octadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

1-0-octadecyl 2-0-acetyl sn-glycero-3-phosphorylcholine: reported to have same biological activity as natural PAF-acether; RN given refers to parent cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2733535
CHEMBL ID1788194
CHEBI ID52450
SCHEMBL ID435191
MeSH IDM0087244
PubMed CID2501
CHEMBL ID12852
MeSH IDM0087244

Synonyms (75)

Synonym
platelet activating factor-acether
1-o-octadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholine
1-o-stearoyl-2-acetyl-sn-glyceryl-3-phosphorylcholine
c18-paf-acether
c18-paf
LMGP01020094
1-octadecyl-2-acetyl-sn-glycero-3-phosphocholine
1-o-octadecyl-2-o-acetyl-sn-glycero-3-phosphocholine
pc(o-18:0/2:0)
ro 14-8161
1-o-octadecyl-platelet-activating factor
NCGC00161375-01
NCGC00161375-02
blood platelet activating factor-aether
3,5,9-trioxo-4-phosphaheptacosan-1-aminium, 7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-, hydroxide, inner salt, 4-oxide, (r)-
1-o-octadecyl-2-o-acetyl-sn-glyceryl-3-phosphorylcholine
NCGC00161375-03
HMS1989I12
(2r)-2-acetoxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate
1-o-octadecyl-paf
74389-69-8
(r)-7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-3,5,9-trioxa-4-phosphaheptaconasan-1-aminium hydroxide inner salt 4-oxide
acetyl-glyceryl-ether-phosphorylcholine
2-o-acetyl-1-o-octadecyl-sn-glycero-3-phosphocholine
c18:0 paf
1-o-stearyl-2-acetyl-sn-glyceryl-3-phosphorylcholine
(-)-1-o-octadeyl-2-o-acetyl-sn-glycerylphosphocholine
1-o-octadecyl-2-acetyl-sn-glycero-3-phosphocholine
1-o-octadecyl 2-o-acetyl sn-glycero-3-phosphorylcholine
CHEBI:52450 ,
phosphatidylcholine (o-18:0/2:0)
(2rr)-2-acetoxy-3-(octadecyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
paf c18
BML3-E05
HMS1361I12
HMS1791I12
[(2r)-2-acetyloxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
CHEMBL1788194
paf(c18)
SCHEMBL435191
1-o-octadecyl-2-acetoyl-sn-glycero-3-phosphocholine
paf c-18
ZXCIEWBDUAPBJF-MUUNZHRXSA-N
HMS3648P16
HMS3402I12
3,5,9-trioxa-4-phosphaheptacosan-1-aminium, 7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-, inner salt, 4-oxide, (r)-
paf (c18)
mfcd00063528
c18-02:0 pc, 1-o-octadecyl-2-acetyl-sn-glycero-3-phosphocholine, powder
c18-02:0 pc, 1-o-octadecyl-2-acetyl-sn-glycero-3-phosphocholine, chloroform
Q60998693
2-chloro-1h-benzimidazole-5-carboxylicacid
DTXSID80995900
2-(acetyloxy)-3-(octadecyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
(r)-2-acetoxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate
1-cis-9-octadecenyl-2-acetyl-sn-glycero-3-phosphocholine
AS-56132
AKOS037645012
C9ZA6E5Q2B
3,5,9-trioxa-4-phosphaheptacosan-1-aminium, 7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-, inner salt, 4-oxide, (7r)-
1-o-octadecyl-platelet activating factor
ro-14-8161
(r)-2-acetoxy-3-(octadecyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
3,5,9-trioxa-4-phosphaheptacosan-1-aminium, 7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-, hydroxide, inner salt, 4-oxide
(+-)-1-o-octadecyl-2-acetylglyceryl-3-phosphorylcholine
1-stearyl-2-o-acetyl-3-glyceryl phosphorylcholine
1-0-octadecyl 2-0-acetyl sn-glycero-3-phosphorylcholine
85733-91-1
platelet activating factor c-18
CHEMBL12852
(2-acetyloxy-3-octadecoxypropyl) 2-(trimethylazaniumyl)ethyl phosphate
FT-0641515
3,5,9-trioxa-4-phosphaheptacosan-1-aminium, 7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-, inner salt, 4-oxide
DTXSID501110671
pc o-18:0_2:0

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The inhibition was shown to be specific and competitive with PAF on its receptor by the following observations: parallel shift of the dose-response curve; crossing of double reciprocal plots on the intersection of the ordinate; and no inhibition on other autacoids such as bradykinin, histamine, 5-hydroxytryptamine and LTC4."( Characterization of the activity of a platelet activating factor antagonist, CV-3988.
Hayashi, M; Kimura, J; Nomura, H; Oh-Ishi, S; Tsushima, S, 1987)		0.27
" Since C18- AGPC suppressed not only the pressor response to noradrenaline but also to angiotensin II and vasopressin, and furthermore, did not disturb the dose-response curve of noradrenaline in the isolated aorta, the possibility of the agent being an alpha-adrenergic antagonist is ruled out."( Mechanism(s) of the hypotensive effect of synthetic 1-O-octadecyl-2-O-acetyl-glycero-3-phosphorylcholine.
Kamitani, T; Katamoto, M; Katsuta, K; Kikuchi, H; Kumada, S; Ono, T; Tatsumi, M, 1984)		0.27
" The time-course and dose-response relationship of the early response has been determined and a synergistic interaction between PAF-acether and prostaglandin E2 established."( Inflammatory characteristics of platelet activating factor (PAF-acether) in human skin.
Archer, CB; MacDonald, DM; Morley, J; Page, CP; Paul, W, 1984)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
hematologic agentDrug that acts on blood and blood-forming organs and those that affect the hemostatic system.
vasodilator agentA drug used to cause dilation of the blood vessels.
bronchoconstrictor agentA drug which causes a narrowing of the lumen of a bronchus or bronchiole.
antihypertensive agentAny drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
beta-adrenergic antagonistAn agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
2-acetyl-1-alkyl-sn-glycero-3-phosphocholineA 2-acyl-1-alkyl-sn-glycero-3-phosphocholine where the 2-O-acyl group is specified as acetyl; a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (8)

PathwayProteinsCompounds
Hemostasis23944
Platelet homeostasis1827
Signaling Pathways1269117
Signaling by GPCR24955
GPCR ligand binding19339
Class A/1 (Rhodopsin-like receptors)16136
GPCR downstream signalling17252
G alpha (q) signalling events7928

Bioassays (32)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID74763Compound was evaluated in anesthetized guinea pigs, for the percentage drop in platelet counts between 2 min before and 1 min after injection at 33 ng/kg1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Structure-activity relationship in PAF-acether. 2. rac-1-O-Octadecyl-2-O-acetyl-3-O-[gamma-(dimethylamino)propyl]glycerol .
AID75944Compound was evaluated for in vivo thrombocytopenia effect in anesthetized guinea pig1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID165610Compound was tested in vitro for its ability to aggregate washed rabbit platelets (WP)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID165607In vitro platelet aggregating activity in washed rabbit platelets1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Structure-activity relationship in PAF-acether. 2. rac-1-O-Octadecyl-2-O-acetyl-3-O-[gamma-(dimethylamino)propyl]glycerol .
AID74005Compound was evaluated for in vivo bronchoconstriction in anesthetized guinea pig (3 cm H2O)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID175321Compound is evaluated for hypotensive activity in anesthetized rat (in vivo)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID165609Compound was tested in vitro for its ability to aggregate platelet-rich plasma (PRP) in rabbit1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID89284Desensitizing action on human PMN degranulation response, in the presence of FMLP (17 nM) at the dose of 60 nM1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Facile synthesis of platelet-activating factor and racemic analogues containing unsaturation in the sn-1-alkyl chain.
AID176023Tested for the molar concentration required to cause 50% of maximum aggregation1984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Analogues of platelet activating factor (PAF). 1. Some modifications of the alkoxy chain.
AID165609Compound was tested in vitro for its ability to aggregate platelet-rich plasma (PRP) in rabbit1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID74009Compound was evaluated in anesthetized guinea pigs, for the percentage decrease of bronchoconstrictive activity1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Structure-activity relationship in PAF-acether. 2. rac-1-O-Octadecyl-2-O-acetyl-3-O-[gamma-(dimethylamino)propyl]glycerol .
AID231444Ratio = (MABP / platelet EC50 ) x 10 E -81984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Analogues of platelet activating factor (PAF). 1. Some modifications of the alkoxy chain.
AID75944Compound was evaluated for in vivo thrombocytopenia effect in anesthetized guinea pig1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID173953Tested for the dose needed to decrease mean arterial blood pressure (MABP) 50 mmHg in male rats, iv1984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Analogues of platelet activating factor (PAF). 1. Some modifications of the alkoxy chain.
AID165607In vitro platelet aggregating activity in washed rabbit platelets1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Structure-activity relationship in PAF-acether. 2. rac-1-O-Octadecyl-2-O-acetyl-3-O-[gamma-(dimethylamino)propyl]glycerol .
AID74005Compound was evaluated for in vivo bronchoconstriction in anesthetized guinea pig (3 cm H2O)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID89292Effective dose for lysozyme release in human PMN was measured1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Facile synthesis of platelet-activating factor and racemic analogues containing unsaturation in the sn-1-alkyl chain.
AID167156Tested for maximum aggregation units at specified molar concentration1984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Analogues of platelet activating factor (PAF). 1. Some modifications of the alkoxy chain.
AID89289Desensitizing action on human PMN degranulation response, in the presence of PAF (200 nM) at the dose of 60 nM1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Facile synthesis of platelet-activating factor and racemic analogues containing unsaturation in the sn-1-alkyl chain.
AID167456Effective dose for [14C]5-HT release in prelabeled rabbit platelets was measured1985Journal of medicinal chemistry, Jan, Volume: 28, Issue:1
Facile synthesis of platelet-activating factor and racemic analogues containing unsaturation in the sn-1-alkyl chain.
AID175321Compound is evaluated for hypotensive activity in anesthetized rat (in vivo)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID161910The maximum aggregation response observed at 1.48e-5 M concentration of the compound1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Analogues of platelet activating factor. 4. Some modifications of the phosphocholine moiety.
AID165636Relative aggregant activity in rabbit platelets was determined1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID165610Compound was tested in vitro for its ability to aggregate washed rabbit platelets (WP)1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Structure-activity relationship in PAF-acether. 3. Hydrophobic contribution to agonistic activity.
AID161909Effective concentration required to produce 50% of maximum aggregation of platelets1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Analogues of platelet activating factor. 4. Some modifications of the phosphocholine moiety.
AID74762Compound was evaluated in anesthetized guinea pigs, for the percentage drop in platelet counts between 2 min before and 1 min after injection1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Structure-activity relationship in PAF-acether. 2. rac-1-O-Octadecyl-2-O-acetyl-3-O-[gamma-(dimethylamino)propyl]glycerol .
AID173774Intravenous dose required to decrease mean arterial blood pressure (MABP) 50 mm Hg1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Analogues of platelet activating factor. 4. Some modifications of the phosphocholine moiety.
AID233534The ratio of (MABP / Platelet EC 50) x 1001986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Analogues of platelet activating factor. 4. Some modifications of the phosphocholine moiety.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-199031 (72.09)18.7374
1990's5 (11.63)18.2507
2000's2 (4.65)29.6817
2010's2 (4.65)24.3611
2020's3 (6.98)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.33

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.33 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.02 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews1 (2.56%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
Other38 (97.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
enantio-PAF C-16
[no description available]		1.9710alkylacylglycero-3-phosphocholine
histamine
[no description available]		1.9610aralkylamino compound;
imidazoles		human metabolite;
mouse metabolite;
neurotransmitter
alprazolam
Alprazolam: A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of PANIC DISORDERS, with or without AGORAPHOBIA, and in generalized ANXIETY DISORDERS. (From AMA Drug Evaluations Annual, 1994, p238). alprazolam : A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individuals that have taken this drug.		1.9710organochlorine compound;
triazolobenzodiazepine		anticonvulsant;
anxiolytic drug;
GABA agonist;
muscle relaxant;
sedative;
xenobiotic
enantio-PAF C-16
[no description available]		2.8840alkylacylglycero-3-phosphocholine
diethylcarbamazine
Diethylcarbamazine: An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.		1.9710N-carbamoylpiperazine;
N-methylpiperazine
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		2.3720aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
isoproterenol
Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.		1.9610catechols;
secondary alcohol;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
cardiotonic drug;
sympathomimetic agent
sodium fluoride
[no description available]		1.9610fluoride saltmutagen
phentolamine
Phentolamine: A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.. phentolamine : A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used for the treatment of hypertension.		2.3620imidazoles;
phenols;
substituted aniline;
tertiary amino compound		alpha-adrenergic antagonist;
vasodilator agent
cyanides
Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.		1.9610pseudohalide anionEC 1.9.3.1 (cytochrome c oxidase) inhibitor
adenosine diphosphate
Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.		2.3720adenosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		fundamental metabolite;
human metabolite
thiazoles
[no description available]		1.97101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
gadolinium
Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.		210f-block element atom;
lanthanoid atom
dazoxiben
dazoxiben: RN given refers to parent cpd		1.9610
web 2086
WEB 2086: structure given in first source; PAF antagonist		2.3820organonitrogen heterocyclic compound;
organosulfur heterocyclic compound
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.38201,2,3-triazole
masoprocol
Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.		1.9710nordihydroguaiaretic acidantineoplastic agent;
hypoglycemic agent;
lipoxygenase inhibitor;
metabolite
nicotine
(S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.		1.99103-(1-methylpyrrolidin-2-yl)pyridineanxiolytic drug;
biomarker;
immunomodulator;
mitogen;
neurotoxin;
nicotinic acetylcholine receptor agonist;
peripheral nervous system drug;
phytogenic insecticide;
plant metabolite;
psychotropic drug;
teratogenic agent;
xenobiotic
fibrinogen
Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.		1.9610iditolfungal metabolite
cv 3988
CV 3988: platelet activating factor antagonist; structure given in first source		2.420
1-hexadecyl-2-acetyl-glycero-3-phosphocholine
Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.		5.933402-acetyl-1-alkyl-sn-glycero-3-phosphocholineantihypertensive agent;
beta-adrenergic antagonist;
bronchoconstrictor agent;
hematologic agent;
vasodilator agent
deoxyglucose
Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.		1.9610
glycerophosphoinositol 4,5-bisphosphate
glycerophosphoinositol 4,5-bisphosphate: do not confuse with phosphatidylinositols which have fatty acids esterified at the C-1 and C-2 hydroxyl groups of glycerol		1.9610
sri 62-834
SRI 62-834: related to ET-18-OCH(3); MLS-266-337 is (R(+))-isomer; structure given in first source		1.9710
angiotensin ii
Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).		1.9610amino acid zwitterion;
angiotensin II		human metabolite
arachidonic acid
icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.		3.5120icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
cotinine
Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.		1.9910N-alkylpyrrolidine;
pyridines;
pyrrolidin-2-ones;
pyrrolidine alkaloid		antidepressant;
biomarker;
human xenobiotic metabolite;
plant metabolite
ovalbumin
Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.		2.0310
dinoprostone
prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.		1.9610prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
leukotriene b4
Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.		1.9610dihydroxy monocarboxylic acid;
hydroxy polyunsaturated fatty acid;
leukotriene;
long-chain fatty acid		human metabolite;
mouse metabolite;
plant metabolite;
vasoconstrictor agent
thromboxane b2
Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.		1.9610thromboxanes Bhuman metabolite;
mouse metabolite
lysophosphatidylcholines
lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.		2.87401-O-acyl-sn-glycero-3-phosphocholine
calcimycin
Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.		2.3720benzoxazole
phosphatidylcholines
Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.		1.97101,2-diacyl-sn-glycero-3-phosphocholine
interleukin-8
Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.		1.9610
guanosine triphosphate
Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.		1.9610guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Constriction, Pathological
[description not available]		02.3720
Thrombopenia
[description not available]		02.3720
Constriction, Pathologic
The condition of an anatomical structure's being constricted beyond normal dimensions.		02.3720
Thrombocytopenia
A subnormal level of BLOOD PLATELETS.		02.3720
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Allergic Conjunctivitis
[description not available]		02.0310
Conjunctivitis, Allergic
Conjunctivitis due to hypersensitivity to various allergens.		02.0310
Decerebrate Posturing
[description not available]		01.9610
Contact Dermatitis
[description not available]		01.9610
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		01.9610
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.		01.9610
Leucocythaemia
[description not available]		01.9610
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		01.9610
Disease Exacerbation
[description not available]		0210
Recrudescence
[description not available]		0210
MS (Multiple Sclerosis)
[description not available]		0210
Multiple Sclerosis
An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)		0210
Acute Promyelocytic Leukemia
[description not available]		01.9710
Animal Mammary Carcinoma
[description not available]		01.9710
Leukemia, Promyelocytic, Acute
An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.		01.9710