azathioprine   Click here for help

GtoPdb Ligand ID: 7120

Synonyms: Azasan® | BW-57-322 | Imuran®
Approved drug Immunopharmacology Ligand
azathioprine is an approved drug (FDA (1968))
Compound class: Synthetic organic
Comment: Azathioprine is an immunosuppressive antimetabolite. The active drug is believed to be mercaptopurine.
Marketed formulations may contain azathioprine sodium (PubChem CID 23678403).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 143.4
Molecular weight 277.04
XLogP 0.67
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Cn1cnc(c1Sc1ncnc2c1nc[nH]2)N(=O)=O
Isomeric SMILES Cn1cnc(c1Sc1ncnc2c1nc[nH]2)N(=O)=O
InChI InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChI Key LMEKQMALGUDUQG-UHFFFAOYSA-N
References
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Characterization of Pharmacologic and Pharmacokinetic Properties of CCX168, a Potent and Selective Orally Administered Complement 5a Receptor Inhibitor, Based on Preclinical Evaluation and Randomized Phase 1 Clinical Study.
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Association of COVID-19 inflammation with activation of the C5a-C5aR1 axis.
Nature, 588 (7836): 146-150. [PMID:32726800]
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New concepts on the therapeutic control of complement anaphylatoxin receptors.
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Protein arginine deiminase 4 (PAD4): Current understanding and future therapeutic potential.
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5. Knuckley B, Luo Y, Thompson PR. (2008)
Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors.
Bioorg Med Chem, 16 (2): 739-45. [PMID:17964793]
6. Li XX, Lee JD, Massey NL, Guan C, Robertson AAB, Clark RJ, Woodruff TM. (2020)
Pharmacological characterisation of small molecule C5aR1 inhibitors in human cells reveals biased activities for signalling and function.
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7. Monk PN, Scola AM, Madala P, Fairlie DP. (2007)
Function, structure and therapeutic potential of complement C5a receptors.
Br J Pharmacol, 152 (4): 429-48. [PMID:17603557]
8. Vlaar APJ, de Bruin S, Busch M, Timmermans SAMEG, van Zeggeren IE, Koning R, Ter Horst L, Bulle EB, van Baarle FEHP, van de Poll MCG et al.. (2020)
Anti-C5a antibody IFX-1 (vilobelimab) treatment versus best supportive care for patients with severe COVID-19 (PANAMO): an exploratory, open-label, phase 2 randomised controlled trial.
Lancet Rheumatol, 2 (12): e764-e773. DOI: 10.1016/S2665-9913(20)30341-6 [PMID:33015643]