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

Stem definition	Drug id	CAS RN
antineoplastic, alkylating agents, (beta-chloroethyl)amine derivatives	512	154-93-8

Description:

Molecule	Description
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

Molecule

Description

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:

Property	Value	Reference
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 µM/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:

Date	Agency	Company	Orphan
March 7, 1977	FDA	EMCURE PHARMS LTD

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (acidic/basic)
pKa1	11.09	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Glutathione reductase, mitochondrial	Enzyme	P00390	GSHR_HUMAN	INHIBITOR	IC50	5.09		CHEMBL	CHEMBL
DNA	DNA			OTHER				DRUG LABEL	DRUG LABEL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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