carmustine 🐶 Veterinary Use | 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
Myelodysplastic syndrome	255.08	38.04	73	2722	15059	50587270
Malignant transformation	139.60	38.04	23	2772	333	50601996
Brain oedema	127.85	38.04	41	2754	12329	50590000
Febrile neutropenia	115.57	38.04	70	2725	97597	50504732
Haematotoxicity	114.75	38.04	34	2761	7861	50594468
Mucosal inflammation	111.56	38.04	51	2744	40091	50562238
Acute myeloid leukaemia	104.45	38.04	37	2758	15037	50587292
Stem cell transplant	82.41	38.04	19	2776	1649	50600680
Second primary malignancy	75.86	38.04	24	2771	6890	50595439
Thrombocytopenia	69.62	38.04	57	2738	127616	50474713
Pneumocephalus	61.26	38.04	10	2785	136	50602193
Enterococcal infection	55.72	38.04	19	2776	6879	50595450
Venoocclusive disease	54.68	38.04	14	2781	1882	50600447
Progressive multifocal leukoencephalopathy	49.77	38.04	20	2775	11437	50590892
Intracranial hypotension	48.86	38.04	9	2786	255	50602074
Chronic myelomonocytic leukaemia	47.62	38.04	9	2786	294	50602035
Cardiomyopathy acute	44.66	38.04	8	2787	193	50602136
Bacteraemia	42.11	38.04	19	2776	14414	50587915
Pneumocystis jirovecii pneumonia	41.82	38.04	19	2776	14644	50587685
Aplasia	40.84	38.04	13	2782	3800	50598529
Neutropenia	40.18	38.04	45	2750	147920	50454409
Febrile bone marrow aplasia	38.08	38.04	14	2781	6297	50596032

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	339.73	32.72	125	5109	17669	29551624
Venoocclusive liver disease	239.53	32.72	76	5158	6841	29562452
Malignant transformation	218.48	32.72	46	5188	788	29568505
Acute myeloid leukaemia	208.43	32.72	86	5148	16427	29552866
Febrile neutropenia	183.00	32.72	154	5080	112086	29457207
Second primary malignancy	134.72	32.72	49	5185	6656	29562637
Brain oedema	122.17	32.72	54	5180	12166	29557127
Pneumocephalus	113.65	32.72	19	5215	81	29569212
Off label use	110.72	32.72	193	5041	300607	29268686
Blood stem cell transplant failure	86.53	32.72	19	5215	399	29568894
Basal cell carcinoma	77.43	32.72	44	5190	16866	29552427
Mucosal inflammation	74.27	32.72	54	5180	31541	29537752
Venoocclusive disease	71.98	32.72	24	5210	2515	29566778
Aspergillus infection	69.46	32.72	35	5199	10546	29558747
Myositis	61.65	32.72	32	5202	10251	29559042
Febrile bone marrow aplasia	59.30	32.72	28	5206	7323	29561970
Transformation to acute myeloid leukaemia	57.20	32.72	15	5219	680	29568613
Malignant neoplasm progression	55.85	32.72	67	5167	73792	29495501
Bronchopulmonary aspergillosis	53.49	32.72	31	5203	12313	29556980
Stem cell transplant	53.22	32.72	18	5216	1969	29567324
Hepatic infection fungal	52.91	32.72	11	5223	176	29569117
Neutropenic sepsis	49.62	32.72	29	5205	11698	29557595
Product use in unapproved indication	47.25	32.72	67	5167	86808	29482485
Metastases to muscle	45.49	32.72	10	5224	211	29569082
Metastases to retroperitoneum	45.22	32.72	10	5224	217	29569076
Enteritis	43.20	32.72	22	5212	6769	29562524
Human herpesvirus 8 infection	40.76	32.72	12	5222	835	29568458
Metastases to spleen	40.10	32.72	10	5224	370	29568923
Cytomegalovirus infection	39.94	32.72	33	5201	23182	29546111
B-cell lymphoma recurrent	39.75	32.72	11	5223	612	29568681
Expanded disability status scale score increased	38.71	32.72	9	5225	246	29569047
Cytopenia	38.10	32.72	23	5211	9836	29559457
Pancytopenia	37.82	32.72	59	5175	83109	29486184
Metastases to bone marrow	37.74	32.72	10	5224	472	29568821
Intracranial hypotension	34.68	32.72	8	5226	211	29569082
Retinal haemorrhage	32.81	32.72	16	5218	4488	29564805
Intentional product use issue	32.80	32.72	39	5195	42459	29526834

FDA Adverse Event Reporting System (Geriatric)

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	544.00	30.53	178	7246	27401	64463907
Malignant transformation	332.50	30.53	64	7360	1077	64490231
Acute myeloid leukaemia	313.19	30.53	118	7306	27345	64463963
Febrile neutropenia	293.95	30.53	211	7213	187446	64303862
Venoocclusive liver disease	256.52	30.53	79	7345	9936	64481372
Brain oedema	223.43	30.53	87	7337	21988	64469320
Second primary malignancy	204.59	30.53	70	7354	12267	64479041
Pneumocephalus	144.75	30.53	25	7399	220	64491088
Mucosal inflammation	134.88	30.53	86	7338	62498	64428810
Haematotoxicity	134.58	30.53	52	7372	12844	64478464
Stem cell transplant	121.93	30.53	35	7389	3446	64487862
Off label use	114.91	30.53	235	7189	632571	63858737
Venoocclusive disease	108.64	30.53	33	7391	3952	64487356
Blood stem cell transplant failure	89.99	30.53	19	7405	516	64490792
Aspergillus infection	75.11	30.53	37	7387	16342	64474966
Pneumocystis jirovecii pneumonia	72.26	30.53	43	7381	27591	64463717
Malignant neoplasm progression	67.99	30.53	74	7350	112797	64378511
Basal cell carcinoma	67.91	30.53	43	7381	30795	64460513
Febrile bone marrow aplasia	65.62	30.53	30	7394	11225	64480083
Thrombocytopenia	64.52	30.53	102	7322	223699	64267609
Cytomegalovirus infection	62.90	30.53	44	7380	37155	64454153
Product use in unapproved indication	61.58	30.53	88	7336	176530	64314778
Myositis	60.56	30.53	32	7392	16345	64474963
Bronchopulmonary aspergillosis	58.68	30.53	33	7391	19052	64472256
Progressive multifocal leukoencephalopathy	57.34	30.53	32	7392	18200	64473108
Aplasia	55.07	30.53	23	7401	6930	64484378
Hemiplegia	53.11	30.53	27	7397	12741	64478567
Pneumonia respiratory syncytial viral	52.85	30.53	15	7409	1416	64489892
Intracranial hypotension	50.57	30.53	11	7413	345	64490963
Neutropenic sepsis	50.11	30.53	32	7392	23240	64468068
B-cell lymphoma recurrent	46.07	30.53	12	7412	820	64490488
Metastases to muscle	45.90	30.53	10	7414	316	64490992
Cytopenia	45.53	30.53	26	7398	15445	64475863
Metastases to retroperitoneum	44.56	30.53	10	7414	363	64490945
Human herpesvirus 8 infection	43.05	30.53	12	7412	1061	64490247
Lymphopenia	42.55	30.53	30	7394	25627	64465681
Metastases to spleen	41.52	30.53	10	7414	496	64490812
Conjunctival haemorrhage	41.08	30.53	17	7407	5004	64486304
Pancytopenia	40.79	30.53	65	7359	143244	64348064
Brain abscess	40.56	30.53	16	7408	4165	64487143
Enterococcal infection	39.99	30.53	23	7401	13843	64477465
Arthralgia	39.57	30.53	3	7421	442257	64049051
Acute respiratory distress syndrome	39.44	30.53	34	7390	38901	64452407
Metastases to bone marrow	38.76	30.53	10	7414	658	64490650
Hepatic infection fungal	38.68	30.53	8	7416	196	64491112
Neutropenia	38.47	30.53	85	7339	239539	64251769
Enteritis	37.43	30.53	21	7403	12056	64479252
Cardiomyopathy acute	37.31	30.53	8	7416	234	64491074
Transformation to acute myeloid leukaemia	36.25	30.53	10	7414	851	64490457
Staphylococcal infection	35.41	30.53	36	7388	50642	64440666
Fatigue	34.42	30.53	22	7402	748708	63742600
Respiratory tract infection fungal	33.90	30.53	10	7414	1082	64490226
Cystitis haemorrhagic	33.59	30.53	17	7407	7939	64483369
Dizziness	33.18	30.53	5	7419	430158	64061150
Chronic myelomonocytic leukaemia	32.85	30.53	9	7415	746	64490562
Human herpesvirus 6 infection	32.23	30.53	14	7410	4640	64486668
Implant site oedema	32.11	30.53	5	7419	21	64491287
Malaise	31.99	30.53	4	7420	396243	64095065
Expanded disability status scale score increased	31.96	30.53	8	7416	466	64490842
Myelosuppression	30.83	30.53	24	7400	23806	64467502
Herpes simplex reactivation	30.78	30.53	7	7417	270	64491038

FDA Adverse Event Reporting System (Pediatric)

None

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
CHEBI has role	CHEBI:35610	antineoplastic agents
MeSH PA	D000477	Alkylating Agents
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D018906	Antineoplastic Agents, Alkylating
MeSH PA	D009676	Noxae

Drug Use | Suggest Off label Use Form| |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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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

External reference:

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

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Gliadel	HUMAN PRESCRIPTION DRUG LABEL	1	24338-050	WAFER	7.70 mg	INTRACAVITARY	NDA	25 sections