carmustine indications/contra

Stem definitionDrug idCAS RN
antineoplastic, alkylating agents, (beta-chloroethyl)amine derivatives 512 154-93-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • carmustine
  • becenun
  • carmubris
  • carmustin
  • nitrumon
A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed)
  • Molecular weight: 214.05
  • Formula: C5H9Cl2N3O2
  • CLOGP: 1.32
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 61.77
  • ALOGS: -2.15
  • ROTB: 5

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
March 7, 1977 FDA EMCURE PHARMS LTD

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Brain oedema 589.17 72.81 109 1024 3695 3381031
Mucosal inflammation 227.81 72.81 57 1076 7926 3376800
Pneumocephalus 227.55 72.81 30 1103 84 3384642
Febrile neutropenia 195.72 72.81 61 1072 18914 3365812
Myelodysplastic syndrome 174.33 72.81 43 1090 5604 3379122
Off label use 162.84 72.81 70 1063 53907 3330819
Hemiplegia 155.94 72.81 33 1100 2165 3382561
Sepsis 145.56 72.81 56 1077 32317 3352409
Infection 132.41 72.81 49 1084 25353 3359373
Intracranial hypotension 131.90 72.81 21 1112 272 3384454
Thrombocytopenia 127.01 72.81 52 1081 35216 3349510
Brain abscess 109.05 72.81 20 1113 619 3384107
Seizure 103.97 72.81 47 1086 40353 3344373
Neutropenia 102.55 72.81 44 1089 33342 3351384
Post procedural complication 99.97 72.81 27 1106 4990 3379736
Pulmonary embolism 99.84 72.81 41 1092 27847 3356879
Hydrocephalus 96.67 72.81 21 1112 1552 3383174
Acute myeloid leukaemia 89.88 72.81 25 1108 5148 3379578
Pyrexia 88.49 72.81 53 1080 81062 3303664
Deep vein thrombosis 85.26 72.81 34 1099 21355 3363371
Cerebrospinal fluid leakage 80.38 72.81 14 1119 320 3384406
Kaposi's sarcoma 78.87 72.81 16 1117 846 3383880
Stem cell transplant 78.82 72.81 16 1117 849 3383877
Cerebral infarction 78.21 72.81 25 1108 8275 3376451
Leukopenia 76.67 72.81 29 1104 15794 3368932
Postoperative wound infection 75.48 72.81 17 1116 1480 3383246
Aphasia 74.36 72.81 23 1110 6838 3377888

Pharmacologic Action:

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SourceCodeDescription
ATC L01AD01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ALKYLATING AGENTS
Nitrosoureas
CHEBI has role CHEBI:35610 antineoplastic agent
FDA MoA N0000000236 Alkylating Activity
FDA EPC N0000175558 Alkylating Drug
MeSH PA D000477 Alkylating Agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018906 Antineoplastic Agents, Alkylating
MeSH PA D009676 Noxae

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Glioma, malignant indication 74532006 DOID:3070
Diffuse non-Hodgkin's lymphoma, large cell indication 109969005
Multiple myeloma indication 109989006 DOID:9538
Hodgkin's disease indication 118599009 DOID:8651
Non-Hodgkin's lymphoma indication 118601006 DOID:8675
Glioblastoma multiforme of brain indication 276828006 DOID:3073
Malignant neoplasm of brain indication 428061005 DOID:1319
Cerebral edema contraindication 2032001 DOID:4724
Mycosis contraindication 3218000 DOID:1564
Meningitis contraindication 7180009 DOID:9471
Disorder of lung contraindication 19829001 DOID:850
Retinal hemorrhage contraindication 28998008
Viral disease contraindication 34014006 DOID:934
Infectious disease contraindication 40733004
Fibrosis of lung contraindication 51615001 DOID:3770
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Bacterial infectious disease contraindication 87628006 DOID:104
Kidney disease contraindication 90708001 DOID:2527
Acute leukemia, disease contraindication 91855006 DOID:12603
Liver function tests abnormal contraindication 166603001
Obstructive hydrocephalus contraindication 230746009 DOID:14159
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Abscess of brain contraindication 441806004
Significant Bleeding contraindication
Protozoal Infection contraindication
Pulmonary Infiltrates contraindication
Astrocytoma, anaplastic off-label use 55353007 DOID:3078
Allogeneic bone marrow transplantation off-label use 58390007
Mycosis fungoides off-label use 118618005 DOID:8691

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.09 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Glutathione reductase, mitochondrial Enzyme INHIBITOR IC50 5.09 CHEMBL CHEMBL
DNA DNA OTHER DRUG LABEL DRUG LABEL

External reference:

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IDSource
DB00262 DRUGBANK_ID
4020993 VUID
N0000148463 NUI
C0007257 UMLSCUI
6800 IUPHAR_LIGAND_ID
D00254 KEGG_DRUG
CHEMBL513 ChEMBL_ID
2578 PUBCHEM_CID
4018136 VANDF
N0000006684 NDFRT
N0000148463 NDFRT
N0000146473 NDFRT
002640 NDDF
2105 RXNORM
387281007 SNOMEDCT_US
51326002 SNOMEDCT_US
4360 MMSL
d01342 MMSL
4020993 VANDF
CHEBI:3423 CHEBI
D002330 MESH_DESCRIPTOR_UI
U68WG3173Y UNII
2959 INN_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
BiCNU HUMAN PRESCRIPTION DRUG LABEL 1 23155-261 KIT 100 mg None NDA 17 sections
Gliadel HUMAN PRESCRIPTION DRUG LABEL 1 24338-050 WAFER 7.70 mg INTRACAVITARY NDA 16 sections