CARMUSTINE

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Trade Names:
Synonyms:
Status: Approved (1977)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L01AD01
UNII: U68WG3173Y

Structure
InChI Key DLGOEMSEDOSKAD-UHFFFAOYSA-N
Smile O=NN(CCCl)C(=O)NCCCl
InChI
InChI=1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)

Physicochemical Descriptors

Property Name Value
Molecular Formula C5H9Cl2N3O2
Molecular Weight 214.05
AlogP 1.16
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 61.77
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 12.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 1.53 - EXP
Henry's Law Constant 4.76E-11 atm-m3/mole EST
Atmospheric OH Rate Constant 3.63E-12 cm3/molecule-sec EST
Melting Point 31 deg C EXP
Water Solubility 4000 mg/L EXP
Vapor Pressure 3.69E-05 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor FDA
Primary Target
glutathione-disulfide reductase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 8100 - - 20
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 107
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 97210 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Glioma 4 D005910 ClinicalTrials
Medulloblastoma 4 D008527 FDA
Astrocytoma 4 D001254 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Glioma 4 D005910 ClinicalTrials
Glioma 4 D005910 ClinicalTrials
Central Nervous System Neoplasms 3 D016543 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Oligodendroglioma 3 D009837 ClinicalTrials
Lymphoma, Mantle-Cell 3 D020522 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 2 D020529 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Lymphoma, T-Cell, Peripheral 2 D016411 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Stiff-Person Syndrome 2 D016750 ClinicalTrials
Neuromyelitis Optica 2 D009471 ClinicalTrials
Myasthenia Gravis 2 D009157 ClinicalTrials
Polyradiculoneuropathy, Chronic Inflammatory Demyelinating 2 D020277 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Opsoclonus-Myoclonus Syndrome 2 D053578 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Leukemia, Plasma Cell 1 D007952 ClinicalTrials
Neuroblastoma 1 D009447 ClinicalTrials
Lymphoma, T-Cell, Cutaneous 1 D016410 ClinicalTrials
Sezary Syndrome 1 D012751 ClinicalTrials
Mycosis Fungoides 1 D009182 ClinicalTrials

Related Entries

MCS

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
22.3
Injury, poisoning and procedural complications
13.45
General disorders and administration site conditions
10.73
Vascular disorders
8.61
Respiratory, thoracic and mediastinal disorders
7.17
Infections and infestations
6.48
Cardiac disorders
4.01
Blood and lymphatic system disorders
3.41
Psychiatric disorders
3.41
Gastrointestinal disorders
2.82
Investigations
2.82
Skin and subcutaneous tissue disorders
2.47
Metabolism and nutrition disorders
2.23
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.03

Cross References

Resources Reference
CAS NUMBER 154-93-8
ChEBI 3423
ChEMBL CHEMBL513
DrugBank DB00262
DrugCentral 512
EPA CompTox DTXSID8022743
FDA SRS U68WG3173Y
Human Metabolome Database HMDB0014407
Guide to Pharmacology 6800
KEGG C06873
PharmGKB PA448810
PubChem 2578
SureChEMBL SCHEMBL4503
ZINC ZINC000003830387
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