8-chloroadenosine profile

8-chloroadenosine: active metabolite of 8-chloro-cyclic adenosine 3',5'-monophosphate [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	147569
CHEMBL ID	4594396
SCHEMBL ID	987728
MeSH ID	M0203289

Synonym
8-chloroadenosine
adenosine, 8-chloro-
nsc-354258
34408-14-5
(2r,3r,4s,5r)-2-(6-amino-8-chloro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
adenosine,8-chloro
2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
(2r,3r,4s,5r)-2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
unii-pa05mfh3i7
nsc 354258
pa05mfh3i7 ,
8-chloro-adenosine
A822226
(2r,3r,4s,5r)-2-(6-amino-8-chloro-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
SCHEMBL987728
AKOS024284395
AC-32299
8-cl-ado
MHDPPLULTMGBSI-UUOKFMHZSA-N
Q27286427
CHEMBL4594396
PD143748

Excerpt	Reference	Relevance
" The main pharmacokinetic parameters of 8-Cl-Ad, t1/2beta and AUC, were 69."	( Determination of pharmacokinetics of 8-chloroadenosine and its two major metabolites in dogs by high-performance liquid chromatography. Lou, Y; Wang, X; Zhang, W; Zou, A, 2000)	0.58
" To improve its pharmacokinetic properties, 8-chloro-adenosine-5'-O-stearate (8CAS), a lipophilic octadecanoyl analogue of 8CA, was synthesized and incorporated into pegylated liposomes."	( A novel approach to improve the pharmacokinetic properties of 8-chloro-adenosine by the dual combination of lipophilic derivatisation and liposome formulation. Jiao, YY; Lu, WL; Wang, XQ; Yang, ZJ; Zhang, Q, 2013)	0.39

Excerpt	Reference	Relevance
" These results indicate that the lipophilic derivation of 8CA and the incorporation of 8CAS is an effective strategy to improve the bioavailability of 8CA."	( A novel approach to improve the pharmacokinetic properties of 8-chloro-adenosine by the dual combination of lipophilic derivatisation and liposome formulation. Jiao, YY; Lu, WL; Wang, XQ; Yang, ZJ; Zhang, Q, 2013)	0.39

Excerpt	Relevance	Reference
" Moreover, the dose-response curves and the IC50 values of the latter compound for the various cell lines were compatible with those observed for 8-Cl-cAMP in fresh serum."	( Effects of 8-chloro-cyclic adenosine monophosphate on the growth and sensitivity to doxorubicin of multidrug-resistant tumour cell lines. Borsellino, N; Crescimanno, M; D'Alessandro, N; Leonardi, V, 1994)	0.29
" 8CA or 8CAS-PL at a dosage of 10mg/kg daily."	( A novel approach to improve the pharmacokinetic properties of 8-chloro-adenosine by the dual combination of lipophilic derivatisation and liposome formulation. Jiao, YY; Lu, WL; Wang, XQ; Yang, ZJ; Zhang, Q, 2013)	0.39

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	12 (20.69)	18.2507
2000's	29 (50.00)	29.6817
2010's	12 (20.69)	24.3611
2020's	5 (8.62)	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	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	60 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2.05	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.07	1	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
go 6976 [no description available]	2.05	1	indolocarbazole; organic heterohexacyclic compound	EC 2.7.11.13 (protein kinase C) inhibitor
hydroxychloroquine Hydroxychloroquine: A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites. Hydroxychloroquine appears to concentrate in food vacuoles of affected protozoa. It inhibits plasmodial heme polymerase. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p970). hydroxychloroquine : An aminoquinoline that is chloroquine in which one of the N-ethyl groups is hydroxylated at position 2. An antimalarial with properties similar to chloroquine that acts against erythrocytic forms of malarial parasites, it is mainly used as the sulfate salt for the treatment of lupus erythematosus, rheumatoid arthritis, and light-sensitive skin eruptions.	2.6	1	aminoquinoline; organochlorine compound; primary alcohol; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; dermatologic drug
1-methyl-3-isobutylxanthine 1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.	2.42	2	3-isobutyl-1-methylxanthine
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.05	1	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
2-methyltetrahydrofuran 2-methyltetrahydrofuran: structure in first source	7.07	1
hexylamine hexylamine: RN given refers to parent cpd; structure. 1-hexanamine : A 6-carbon primary aliphatic amine.	2.13	1	primary aliphatic amine	metabolite
2-chloroadenosine 5-chloroformycin A: structure given in first source	5.39	57	purine nucleoside
8-bromo cyclic adenosine monophosphate 8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.	4.35	20	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	3.18	5	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
4-nitrobenzylthioinosine 4-nitrobenzylthioinosine: inhibitor of nucleoside transport; acts on ENT1	1.99	1	purine nucleoside
8-azaadenosine [no description available]	7.31	1	N-glycosyl compound
8-aminoadenosine [no description available]	2.07	1
8-chloro-cyclic adenosine monophosphate [no description available]	9.35	20
sulfinosine sulfinosine: structure given in first source	2.03	1
pentostatin Pentostatin: A potent inhibitor of ADENOSINE DEAMINASE. The drug induces APOPTOSIS of LYMPHOCYTES, and is used in the treatment of many lymphoproliferative malignancies, particularly HAIRY CELL LEUKEMIA. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity.. pentostatin : A member of the class of coformycins that is coformycin in which the hydroxy group at position 2' is replaced with a hydrogen. It is a drug used for the treatment of hairy cell leukaemia.	2.01	1	coformycins	antimetabolite; antineoplastic agent; Aspergillus metabolite; bacterial metabolite; EC 3.5.4.4 (adenosine deaminase) inhibitor
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	2.02	1	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
thioinosine Thioinosine: Sulfhydryl analog of INOSINE that inhibits nucleoside transport across erythrocyte plasma membranes, and has immunosuppressive properties. It has been used similarly to MERCAPTOPURINE in the treatment of leukemia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p503)	1.99	1
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	2.02	1	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.05	1	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
adenosine kinase Adenosine Kinase: An enzyme that catalyzes the formation of ADP plus AMP from adenosine plus ATP. It can serve as a salvage mechanism for returning adenosine to nucleic acids. EC 2.7.1.20.	2.7	3
piperidines Piperidines: A family of hexahydropyridines.	2.13	1
abt-199 venetoclax: A BCL-2 inhibitor with antineoplastic activity that is used in the treatment of CHRONIC LYMPHOCYTIC LEUKEMIA associated with chromosome 17p deletion; structure in first source.. venetoclax : A member of the class of pyrrolopyridines that is a potent inhibitor of the antiapoptotic protein B-cell lymphoma 2. It is used for treamtment of chronic lymphocytic leukemia with 17p deletion.	2.31	1	aromatic ether; C-nitro compound; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; N-sulfonylcarboxamide; oxanes; pyrrolopyridine	antineoplastic agent; apoptosis inducer; B-cell lymphoma 2 inhibitor
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	7.03	1
oligomycins Oligomycins: A closely related group of toxic substances elaborated by various strains of Streptomyces. They are 26-membered macrolides with lactone moieties and double bonds and inhibit various ATPases, causing uncoupling of phosphorylation from mitochondrial respiration. Used as tools in cytochemistry. Some specific oligomycins are RUTAMYCIN, peliomycin, and botrycidin (formerly venturicidin X).	2.05	1
inosine [no description available]	2.01	1	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite

Condition	Indicated	Relationship Strength	Studies
Carcinoma, Non-Small Cell Lung [description not available]	0	2.41	1
Cancer of Lung [description not available]	0	3.3	6
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	0	2.41	1
Lung Neoplasms Tumors or cancer of the LUNG.	0	3.3	6
Cholangiocellular Carcinoma [description not available]	0	2.6	1
Bile Duct Cancer [description not available]	0	2.6	1
Bile Duct Neoplasms Tumors or cancer of the BILE DUCTS.	0	2.6	1
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	0	7.6	1
Acute Myelogenous Leukemia [description not available]	0	2.31	1
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	1	4.31	1
Tetraploid [description not available]	0	2.08	1
Abnormalities, Autosome [description not available]	0	2.08	1
Breast Cancer [description not available]	0	7.74	3
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	0	2.1	1
Breast Neoplasms Tumors or cancer of the human BREAST.	0	2.74	3
Cancer of the Thyroid [description not available]	0	2.48	2
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	0	2.48	2
Carcinoma, Neuroendocrine A group of carcinomas which share a characteristic morphology, often being composed of clusters and trabecular sheets of round blue cells, granular chromatin, and an attenuated rim of poorly demarcated cytoplasm. Neuroendocrine tumors include carcinoids, small (oat) cell carcinomas, medullary carcinoma of the thyroid, Merkel cell tumor, cutaneous neuroendocrine carcinoma, pancreatic islet cell tumors, and pheochromocytoma. Neurosecretory granules are found within the tumor cells. (Segen, Dictionary of Modern Medicine, 1992)	0	2.13	1
Adenocarcinoma Of Kidney [description not available]	0	2.11	1
Cancer of Kidney [description not available]	0	2.11	1
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	0	2.11	1
Kidney Neoplasms Tumors or cancers of the KIDNEY.	0	2.11	1
Granulocytic Leukemia [description not available]	0	2.05	1
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	0	2.05	1
Diffuse Lymphocytic Lymphoma, Poorly-Differentiated [description not available]	0	2.75	3
Lymphoma, Mantle-Cell A form of non-Hodgkin lymphoma having a usually diffuse pattern with both small and medium lymphocytes and small cleaved cells. It accounts for about 5% of adult non-Hodgkin lymphomas in the United States and Europe. The majority of mantle-cell lymphomas are associated with a t(11;14) translocation resulting in overexpression of the CYCLIN D1 gene (GENES, BCL-1).	0	2.75	3
Lung Adenocarcinoma [description not available]	0	2.07	1
Adenocarcinoma, Basal Cell [description not available]	0	2.41	2
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	0	2.07	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	0	2.41	2
Hematologic Malignancies [description not available]	0	2.07	1
Kahler Disease [description not available]	0	3.12	5
B-Cell Chronic Lymphocytic Leukemia [description not available]	0	2.07	1
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	0	3.12	5
Leukemia, Lymphocytic, Chronic, B-Cell A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.	0	2.07	1
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	0	2.07	1
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	0	7.42	2
Hepatocellular Carcinoma [description not available]	0	2.42	2
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	0	2.42	2
Cancer of Liver [description not available]	0	2.02	1
Liver Neoplasms Tumors or cancer of the LIVER.	0	2.02	1
Leukemia L 1210 [description not available]	0	1.98	1
Experimental Hepatoma [description not available]	0	1.98	1
Cancer of Stomach [description not available]	0	2.39	2
Stomach Neoplasms Tumors or cancer of the STOMACH.	0	2.39	2
B16 Melanoma [description not available]	0	1.98	1
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)	0	1.98	1
Benign Neoplasms [description not available]	0	1.99	1
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.	0	1.99	1
Carcinoma, Colloid [description not available]	0	1.99	1
Adenocarcinoma, Mucinous An adenocarcinoma producing mucin in significant amounts. (From Dorland, 27th ed)	0	1.99	1
Leukemia, Lymphocytic, T Cell [description not available]	0	2	1
Leukemia, T-Cell A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.	0	2	1
Cancer of Colon [description not available]	0	1.98	1
Colonic Neoplasms Tumors or cancer of the COLON.	0	1.98	1
Glial Cell Tumors [description not available]	0	1.98	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	0	6.98	1

8-chloroadenosine

Description

Cross-References

Synonyms (22)

Research Excerpts

Pharmacokinetics

Bioavailability

Dosage Studied

Research

Studies (58)

Market Indicators

Research Demand Index: 24.89

Study Types

8-chloroadenosine

Description

Cross-References

Synonyms (22)

Research Excerpts

Pharmacokinetics

Bioavailability

Dosage Studied

Research

Studies (58)

Market Indicators

Research Demand Index: 24.89

Study Types

Related Drugs (27)

Related Conditions (57)