cyclophosphamide   Click here for help

GtoPdb Ligand ID: 7154

Synonyms: cytophosphane | Cytoxan® | Endoxan®
Approved drug
cyclophosphamide is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Cyclophosphamide is an alkylating agent of the nitrogen mustard type. It is converted in vivo to the active metabolite 4-hydroxy cyclophosphamide by liver cytochrome P450 (CYP) enzymes. It is used mainly as a cancer chemotherapeutic. It can be used to treat autoimmune conditions, but as it has severe and life-threatening side-effects, other less toxic medications may be the preferred option following an acuteautoimmune crisis.
Cyclophosphamide is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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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 5
Topological polar surface area 51.38
Molecular weight 260.02
XLogP 0.83
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES ClCCN(P1(=O)NCCCO1)CCCl
Isomeric SMILES ClCCN(P1(=O)NCCCO1)CCCl
InChI InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
InChI Key CMSMOCZEIVJLDB-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.
PLoS ONE, 11 (10): e0164646. [PMID:27768695]
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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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Pharmacological characterisation of small molecule C5aR1 inhibitors in human cells reveals biased activities for signalling and function.
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5. Monk PN, Scola AM, Madala P, Fairlie DP. (2007)
Function, structure and therapeutic potential of complement C5a receptors.
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6. 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]