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	251.59	39.83	73	3244	16681	63469024
Malignant transformation	137.23	39.83	23	3294	394	63485311
Mucosal inflammation	134.81	39.83	60	3257	46868	63438837
Febrile neutropenia	131.77	39.83	80	3237	118369	63367336
Brain oedema	124.50	39.83	41	3276	14154	63471551
Haematotoxicity	110.82	39.83	34	3283	9342	63476363
Acute myeloid leukaemia	101.77	39.83	37	3280	17110	63468595
Diffuse large B-cell lymphoma recurrent	82.30	39.83	20	3297	2300	63483405
Second primary malignancy	82.06	39.83	26	3291	7927	63477778
Stem cell transplant	81.78	39.83	19	3298	1803	63483902
Pneumonia adenoviral	76.44	39.83	12	3305	133	63485572
Thrombocytopenia	69.98	39.83	60	3257	151097	63334608
Gastroenteritis adenovirus	69.49	39.83	12	3305	247	63485458
Adenovirus infection	69.09	39.83	19	3298	3552	63482153
Adenoviral hepatitis	64.25	39.83	12	3305	389	63485316
Thrombotic microangiopathy	63.42	39.83	23	3294	10538	63475167
Pneumocephalus	59.72	39.83	10	3307	170	63485535
Enterococcal infection	58.21	39.83	20	3297	7828	63477877
Venoocclusive disease	54.30	39.83	14	3303	2044	63483661
Human herpesvirus 6 infection	53.82	39.83	15	3302	2942	63482763
Septic shock	49.41	39.83	35	3282	66594	63419111
Progressive multifocal leukoencephalopathy	48.43	39.83	20	3297	12951	63472754
Intracranial hypotension	48.09	39.83	9	3308	295	63485410
Chronic myelomonocytic leukaemia	47.11	39.83	9	3308	330	63485375
Gastric cancer	46.89	39.83	15	3302	4708	63480997
Cardiomyopathy acute	42.96	39.83	8	3309	255	63485450
Cytomegalovirus infection reactivation	41.05	39.83	13	3304	3950	63481755
Pneumocystis jirovecii pneumonia	40.23	39.83	19	3298	16895	63468810
Aplasia	40.13	39.83	13	3304	4246	63481459

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	334.51	30.83	125	5848	19083	34931875
Venoocclusive liver disease	260.10	30.83	83	5890	7883	34943075
Acute myeloid leukaemia	219.67	30.83	91	5882	18179	34932779
Malignant transformation	219.14	30.83	46	5927	805	34950153
Febrile neutropenia	170.73	30.83	159	5814	136690	34814268
Second primary malignancy	150.59	30.83	55	5918	7831	34943127
Off label use	143.16	30.83	255	5718	419269	34531689
Brain oedema	120.74	30.83	55	5918	13766	34937192
Pneumocephalus	104.58	30.83	19	5954	148	34950810
Blood stem cell transplant failure	87.01	30.83	19	5954	403	34950555
Mucosal inflammation	83.75	30.83	62	5911	38560	34912398
Disease progression	82.88	30.83	97	5876	107980	34842978
Basal cell carcinoma	75.28	30.83	45	5928	19613	34931345
Venoocclusive disease	73.85	30.83	25	5948	2842	34948116
Aspergillus infection	68.59	30.83	36	5937	12218	34938740
Myositis	66.26	30.83	35	5938	12035	34938923
Malignant neoplasm progression	62.46	30.83	76	5897	87970	34862988
Neutropenic sepsis	59.25	30.83	34	5939	13733	34937225
Febrile bone marrow aplasia	57.29	30.83	28	5945	8181	34942777
Transformation to acute myeloid leukaemia	56.12	30.83	15	5958	759	34950199
Bronchopulmonary aspergillosis	54.67	30.83	33	5940	14626	34936332
Neutropenic colitis	52.91	30.83	20	5953	3124	34947834
Progressive multifocal leukoencephalopathy	52.70	30.83	28	5945	9736	34941222
Hepatic infection fungal	52.62	30.83	11	5962	188	34950770
Stem cell transplant	52.54	30.83	18	5955	2121	34948837
Pancytopenia	45.78	30.83	68	5905	95089	34855869
Product use in unapproved indication	45.51	30.83	76	5897	117423	34833535
Metastases to muscle	44.81	30.83	10	5963	235	34950723
Metastases to retroperitoneum	44.37	30.83	10	5963	246	34950712
B-cell lymphoma recurrent	41.79	30.83	12	5961	792	34950166
Enteritis	40.17	30.83	22	5951	8120	34942838
Haematotoxicity	40.04	30.83	22	5951	8172	34942786
Cytomegalovirus infection	39.56	30.83	34	5939	26101	34924857
Human herpesvirus 8 infection	39.50	30.83	12	5961	963	34949995
Lymphoma	38.67	30.83	25	5948	12482	34938476
Metastases to spleen	38.35	30.83	10	5963	459	34950499
Metastases to bone marrow	36.99	30.83	10	5963	528	34950430
Pneumocystis jirovecii pneumonia	36.86	30.83	29	5944	19681	34931277
Expanded disability status scale score increased	36.53	30.83	9	5964	328	34950630
Cytopenia	35.85	30.83	24	5949	12699	34938259
Myelosuppression	35.29	30.83	28	5945	19237	34931721
Lymphadenopathy	35.12	30.83	33	5940	28430	34922528
Terminal ileitis	34.47	30.83	8	5965	225	34950733
Retinal haemorrhage	34.43	30.83	17	5956	5072	34945886
Peritoneal lesion	34.34	30.83	7	5966	105	34950853
Therapy partial responder	34.18	30.83	21	5952	9595	34941363
Intracranial hypotension	34.10	30.83	8	5965	236	34950722
Pulmonary toxicity	31.40	30.83	17	5956	6130	34944828
Hydrocephalus	31.07	30.83	16	5957	5216	34945742

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	540.35	30.82	178	8339	30123	79705748
Malignant transformation	333.07	30.82	64	8453	1154	79734717
Acute myeloid leukaemia	326.24	30.82	123	8394	30762	79705109
Febrile neutropenia	303.88	30.82	227	8290	230772	79505099
Venoocclusive liver disease	279.07	30.82	86	8431	11685	79724186
Second primary malignancy	230.40	30.82	78	8439	14272	79721599
Brain oedema	221.79	30.82	88	8429	25175	79710696
Mucosal inflammation	167.87	30.82	103	8414	75477	79660394
Haematotoxicity	153.61	30.82	59	8458	15460	79720411
Off label use	151.32	30.82	311	8206	906904	78828967
Pneumocephalus	137.43	30.82	25	8492	329	79735542
Stem cell transplant	122.36	30.82	35	8482	3669	79732202
Venoocclusive disease	110.82	30.82	34	8483	4539	79731332
Progressive multifocal leukoencephalopathy	93.12	30.82	45	8472	20555	79715316
Blood stem cell transplant failure	91.41	30.82	19	8498	516	79735355
Diffuse large B-cell lymphoma recurrent	88.20	30.82	28	8489	4179	79731692
Pneumocystis jirovecii pneumonia	79.04	30.82	47	8470	32461	79703410
Malignant neoplasm progression	78.23	30.82	84	8433	135906	79599965
Aspergillus infection	78.08	30.82	39	8478	19122	79716749
Thrombocytopenia	72.08	30.82	113	8404	265146	79470725
Myositis	66.47	30.82	35	8482	19133	79716738
Basal cell carcinoma	65.68	30.82	44	8473	37331	79698540
Neutropenic colitis	64.80	30.82	24	8493	5683	79730188
Bronchopulmonary aspergillosis	64.22	30.82	36	8481	22258	79713613
Disease progression	63.72	30.82	88	8429	184274	79551597
Febrile bone marrow aplasia	63.58	30.82	30	8487	12990	79722881
Cytomegalovirus infection	62.73	30.82	45	8472	42599	79693272
Enterococcal infection	61.23	30.82	31	8486	15629	79720242
Product use in unapproved indication	56.33	30.82	98	8419	250261	79485610
Gastroenteritis adenovirus	56.29	30.82	12	8505	369	79735502
Human herpesvirus 6 infection	55.21	30.82	21	8496	5349	79730522
Aplasia	54.12	30.82	23	8494	7797	79728074
Pneumonia adenoviral	52.76	30.82	12	8505	500	79735371
Septic shock	52.31	30.82	65	8452	122736	79613135
Hemiplegia	51.01	30.82	27	8490	14912	79720959
Pneumonia respiratory syncytial viral	49.84	30.82	15	8502	1875	79733996
Intracranial hypotension	49.68	30.82	11	8506	405	79735466
B-cell lymphoma recurrent	49.54	30.82	13	8504	987	79734884
Neutropenic sepsis	47.88	30.82	32	8485	27032	79708839
Pancytopenia	46.89	30.82	72	8445	165673	79570198
Arthralgia	46.36	30.82	4	8513	571799	79164072
Adenoviral hepatitis	45.68	30.82	12	8505	915	79734956
Metastases to muscle	45.65	30.82	10	8507	350	79735521
Acute graft versus host disease	45.30	30.82	22	8495	10145	79725726
Metastases to retroperitoneum	44.51	30.82	10	8507	394	79735477
Fatigue	44.50	30.82	22	8495	929705	78806166
Cytopenia	43.20	30.82	27	8490	20356	79715515
Brain abscess	42.59	30.82	17	8500	4919	79730952
Human herpesvirus 8 infection	42.41	30.82	12	8505	1208	79734663
Therapy partial responder	41.87	30.82	25	8492	17372	79718499
Disease recurrence	39.96	30.82	35	8482	44074	79691797
Metastases to spleen	39.87	30.82	10	8507	634	79735237
Lymphopenia	39.86	30.82	30	8487	30527	79705344
Adenovirus infection	39.82	30.82	19	8498	8428	79727443
Conjunctival haemorrhage	39.76	30.82	17	8500	5848	79730023
Multiple organ dysfunction syndrome	39.42	30.82	56	8461	120190	79615681
Dizziness	39.28	30.82	5	8512	526436	79209435
Malaise	38.17	30.82	4	8513	489865	79246006
Hepatic infection fungal	38.04	30.82	8	8509	230	79735641
Acute respiratory distress syndrome	37.99	30.82	34	8483	44033	79691838
Pulmonary toxicity	37.58	30.82	21	8496	12893	79722978
Metastases to bone marrow	37.45	30.82	10	8507	812	79735059
Pain	36.21	30.82	15	8502	703787	79032084
Cardiomyopathy acute	35.61	30.82	8	8509	315	79735556
Transformation to acute myeloid leukaemia	35.54	30.82	10	8507	987	79734884
Neutropenia	35.51	30.82	88	8429	287622	79448249
Enteritis	35.21	30.82	21	8496	14562	79721309
Myelosuppression	34.56	30.82	31	8486	40265	79695606
Thrombotic microangiopathy	33.65	30.82	23	8494	20146	79715725
Respiratory tract infection fungal	33.60	30.82	10	8507	1203	79734668
Staphylococcal infection	33.45	30.82	36	8481	58259	79677612
Cystitis haemorrhagic	32.51	30.82	17	8500	9155	79726716
Chronic myelomonocytic leukaemia	32.30	30.82	9	8508	857	79735014
Dyspnoea	31.82	30.82	27	8490	856998	78878873
Lymphoma	31.74	30.82	21	8496	17439	79718432
Ureteric compression	31.15	30.82	7	8510	276	79735595
Implant site oedema	31.14	30.82	5	8512	29	79735842

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

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