carmustine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 3.80 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.55 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 11.50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 78 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.23 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.37 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 7, 1977 FDA EMCURE PHARMS LTD

FDA Adverse Event Reporting System (Female)

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 225.37 69.03 40 370 2270 2355405
Myelodysplastic syndrome 120.03 69.03 24 386 2536 2355139
Febrile neutropenia 104.15 69.03 28 382 10854 2346821
Malignant transformation 99.98 69.03 12 398 33 2357642
Pneumocephalus 88.27 69.03 11 399 45 2357630
Mucosal inflammation 71.94 69.03 18 392 5206 2352469

FDA Adverse Event Reporting System (Male)

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
Myelodysplastic syndrome 262.22 75.42 58 704 3231 1742788
Brain oedema 261.88 75.42 54 708 2142 1743877
Off label use 225.47 75.42 89 673 38482 1707537
Malignant transformation 195.75 75.42 26 736 45 1745974
Febrile neutropenia 192.20 75.42 58 704 11042 1734977
Basal cell carcinoma 165.92 75.42 38 724 2445 1743574
Pneumocephalus 154.77 75.42 21 741 46 1745973
Venoocclusive liver disease 146.92 75.42 29 733 904 1745115
Acute myeloid leukaemia 137.74 75.42 34 728 3007 1743012
Neutropenic sepsis 95.01 75.42 22 740 1470 1744549
Cytomegalovirus infection 91.47 75.42 25 737 3276 1742743
Mucosal inflammation 90.15 75.42 26 736 4143 1741876
Pneumocystis jirovecii pneumonia 88.96 75.42 23 739 2433 1743586
Malignant neoplasm progression 82.72 75.42 33 729 14125 1731894
Cytopenia 76.89 75.42 17 745 919 1745100

Pharmacologic Action:

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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Glioma, malignant indication 74532006
Diffuse non-Hodgkin's lymphoma, large cell indication 109969005
Multiple myeloma indication 109989006 DOID:9538
Hodgkin's disease indication 118599009
Non-Hodgkin's lymphoma indication 118601006
Glioblastoma multiforme of brain indication 276828006 DOID:3073
Malignant neoplasm of brain indication 428061005 DOID:1319
Astrocytoma, anaplastic off-label use 55353007 DOID:3078
Allogeneic bone marrow transplantation off-label use 58390007
Mycosis fungoides off-label use 118618005
Cerebral edema contraindication 2032001
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
Kidney disease contraindication 90708001 DOID:557
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
Protozoal Infection contraindication
Significant Bleeding contraindication
Pulmonary Infiltrates contraindication

Acid dissociation constants calculated using MoKa v3.0.0

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:

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:

IDSource
D002330 MESH_DESCRIPTOR_UI
4020993 VUID
N0000148463 NUI
C0007257 UMLSCUI
D00254 KEGG_DRUG
251354 MMSL
51326002 SNOMEDCT_US
786790001 SNOMEDCT_US
4018136 VANDF
002640 NDDF
2105 RXNORM
387281007 SNOMEDCT_US
4360 MMSL
d01342 MMSL
4020993 VANDF
2578 PUBCHEM_CID
CHEBI:3423 CHEBI
CHEMBL513 ChEMBL_ID
DB00262 DRUGBANK_ID
U68WG3173Y UNII
2959 INN_ID
6800 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
BiCNU HUMAN PRESCRIPTION DRUG LABEL 1 23155-261 KIT 100 mg None NDA 17 sections
CARMUSTINE HUMAN PRESCRIPTION DRUG LABEL 1 23155-649 KIT 100 mg None NDA authorized generic 17 sections
Gliadel HUMAN PRESCRIPTION DRUG LABEL 1 24338-050 WAFER 7.70 mg INTRACAVITARY NDA 16 sections
Carmustine HUMAN PRESCRIPTION DRUG LABEL 1 54879-036 KIT 100 mg None ANDA 17 sections
Carmustine HUMAN PRESCRIPTION DRUG LABEL 1 68475-503 KIT 100 mg None ANDA 17 sections
carmustine HUMAN PRESCRIPTION DRUG LABEL 1 70121-1482 KIT 100 mg None ANDA 18 sections
carmustine HUMAN PRESCRIPTION DRUG LABEL 1 70710-1525 KIT 100 mg None ANDA 17 sections