carmustine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT2,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3B,ITK,JAK2,MAP2K6,MAP3K21,MAP3K7,MAPK7,MAPKAPK2,NTRK2,PDK1,PDK2,PDK4,PIK3CB,PIK3CG,PIM2,PLK1,PRKDC,SIK2,SIK3,STK33,SYK,TEK 41
kinase-selectivity-class AXL,BRAF,CDK9,EPHB4,GRK2,MAPK7,STK33,TEK 8
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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
Myelodysplastic syndrome 311.16 42.50 88 4089 20815 90603455
Febrile neutropenia 183.42 42.50 105 4072 158244 90466026
Malignant transformation 179.71 42.50 30 4147 572 90623698
Mucosal inflammation 172.15 42.50 73 4104 57552 90566718
Acute myeloid leukaemia 122.04 42.50 43 4134 20597 90603673
Haematotoxicity 121.82 42.50 38 4139 12497 90611773
Brain oedema 121.34 42.50 41 4136 17344 90606926
Pneumonia adenoviral 92.79 42.50 15 4162 232 90624038
Second primary malignancy 86.52 42.50 28 4149 10350 90613920
Diffuse large B-cell lymphoma recurrent 86.20 42.50 22 4155 3504 90620766
Thrombocytopenia 85.05 42.50 73 4104 208652 90415618
Adenoviral hepatitis 83.74 42.50 15 4162 437 90623833
Disease progression 81.08 42.50 63 4114 156552 90467718
Adenovirus infection 80.29 42.50 22 4155 4600 90619670
Stem cell transplant 75.74 42.50 18 4159 2136 90622134
Gastroenteritis adenovirus 75.65 42.50 13 4164 296 90623974
JC virus infection 66.63 42.50 17 4160 2702 90621568
Septic shock 64.51 42.50 43 4134 84117 90540153
Febrile bone marrow aplasia 64.13 42.50 22 4155 9716 90614554
Progressive multifocal leukoencephalopathy 60.89 42.50 24 4153 15631 90608639
Thrombotic microangiopathy 60.76 42.50 24 4153 15719 90608551
Bacteraemia 59.10 42.50 26 4151 22274 90601996
Acute respiratory distress syndrome 58.89 42.50 28 4149 28658 90595612
Venoocclusive disease 58.45 42.50 15 4162 2440 90621830
Pneumocephalus 56.95 42.50 10 4167 259 90624011
Enterococcal infection 55.93 42.50 20 4157 9971 90614299
Anal squamous cell carcinoma 53.83 42.50 11 4166 650 90623620
Human herpesvirus 6 infection 53.47 42.50 15 4162 3417 90620853
Gastric cancer 51.68 42.50 16 4161 5120 90619150
Lymphoma 49.94 42.50 20 4157 13571 90610699
Intracranial hypotension 48.02 42.50 9 4168 338 90623932
Colitis 47.09 42.50 33 4144 69909 90554361
Aplasia 46.86 42.50 14 4163 3977 90620293
Chronic myelomonocytic leukaemia 46.39 42.50 9 4168 407 90623863
Blood stem cell transplant failure 45.20 42.50 8 4169 217 90624053
Disease recurrence 43.49 42.50 25 4152 37628 90586642
Cardiomyopathy acute 43.01 42.50 8 4169 288 90623982

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 394.14 30.27 147 7046 22598 42591544
Venoocclusive liver disease 251.74 30.27 86 7107 10216 42603926
Second primary malignancy 249.97 30.27 84 7109 9491 42604651
Acute myeloid leukaemia 249.19 30.27 105 7088 22151 42591991
Malignant transformation 230.30 30.27 49 7144 929 42613213
Febrile neutropenia 200.28 30.27 198 6995 185505 42428637
Disease progression 161.77 30.27 157 7036 143499 42470643
Off label use 134.88 30.27 316 6877 638019 41976123
Brain oedema 112.60 30.27 55 7138 16272 42597870
Blood stem cell transplant failure 101.73 30.27 22 7171 451 42613691
Pneumocephalus 101.68 30.27 19 7174 178 42613964
Mucosal inflammation 100.66 30.27 76 7117 49298 42564844
Myositis 78.97 30.27 42 7151 14824 42599318
Diffuse large B-cell lymphoma recurrent 75.13 30.27 29 7164 4857 42609285
Basal cell carcinoma 69.75 30.27 45 7148 22688 42591454
Venoocclusive disease 66.54 30.27 25 7168 3890 42610252
Transformation to acute myeloid leukaemia 64.46 30.27 18 7175 1087 42613055
Malignant neoplasm progression 64.17 30.27 85 7108 108315 42505827
Aspergillus infection 60.37 30.27 36 7157 15801 42598341
Neutropenic sepsis 57.55 30.27 35 7158 15911 42598231
Neutropenic colitis 52.99 30.27 22 7171 4448 42609694
Haematotoxicity 52.66 30.27 29 7164 10956 42603186
Febrile bone marrow aplasia 51.91 30.27 28 7165 10153 42603989
Progressive multifocal leukoencephalopathy 51.33 30.27 29 7164 11507 42602635
Metastatic lymphoma 49.86 30.27 12 7181 401 42613741
Stem cell transplant 48.84 30.27 18 7175 2654 42611488
Human herpesvirus 8 infection 46.53 30.27 15 7178 1482 42612660
B-cell lymphoma recurrent 45.56 30.27 13 7180 849 42613293
Metastases to muscle 44.69 30.27 10 7183 241 42613901
Product use in unapproved indication 44.68 30.27 97 7096 184359 42429783
Bronchopulmonary aspergillosis 44.24 30.27 32 7161 19397 42594745
Hepatic infection fungal 44.11 30.27 10 7183 256 42613886
Metastases to retroperitoneum 43.89 30.27 10 7183 262 42613880
Lymphadenopathy 42.19 30.27 39 7154 33326 42580816
Pancytopenia 42.06 30.27 73 7120 117670 42496472
Cytomegalovirus infection 41.31 30.27 38 7155 32268 42581874
Myelosuppression 41.21 30.27 42 7151 40419 42573723
Intentional product use issue 40.42 30.27 55 7138 71778 42542364
Therapy partial responder 38.94 30.27 30 7163 19991 42594151
Pleuroparenchymal fibroelastosis 37.92 30.27 8 7185 145 42613997
Metastases to spleen 37.66 30.27 10 7183 499 42613643
Peritoneal lesion 37.66 30.27 8 7185 150 42613992
Ureteric compression 37.36 30.27 9 7184 302 42613840
Metastases to bone marrow 36.86 30.27 10 7183 542 42613600
Lymphoma 35.86 30.27 25 7168 14296 42599846
Cytopenia 35.75 30.27 27 7166 17470 42596672
Engraftment syndrome 35.46 30.27 12 7181 1378 42612764
Enteritis 34.62 30.27 22 7171 10794 42603348
Dyspnoea 34.29 30.27 16 7177 442605 42171537
Expanded disability status scale score increased 33.98 30.27 9 7184 445 42613697
Cytomegalovirus infection reactivation 33.95 30.27 22 7171 11156 42602986
Fatigue 33.35 30.27 16 7177 435625 42178517
Metastases to chest wall 33.02 30.27 8 7185 275 42613867
Pneumocystis jirovecii pneumonia 32.93 30.27 30 7163 25151 42588991
Stomatitis 32.11 30.27 41 7152 50288 42563854
Neoplasm progression 31.17 30.27 31 7162 28969 42585173
Staphylococcal infection 31.14 30.27 35 7158 37608 42576534
Thrombocytopenia 31.04 30.27 86 7107 190193 42423949
Ill-defined disorder 30.78 30.27 24 7169 16272 42597870
Mantle cell lymphoma recurrent 30.77 30.27 10 7183 1013 42613129
Hepatic angiosarcoma 30.45 30.27 6 7187 76 42614066

FDA Adverse Event Reporting System (Geriatric)

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 624.29 31.61 203 10248 37281 110541567
Febrile neutropenia 406.35 31.61 292 10159 316475 110262373
Acute myeloid leukaemia 387.99 31.61 143 10308 37967 110540881
Malignant transformation 382.01 31.61 73 10378 1452 110577396
Second primary malignancy 296.99 31.61 97 10354 17971 110560877
Venoocclusive liver disease 275.89 31.61 88 10363 15119 110563729
Brain oedema 214.43 31.61 88 10363 31010 110547838
Mucosal inflammation 212.43 31.61 125 10326 96016 110482832
Haematotoxicity 192.12 31.61 73 10378 21009 110557839
Off label use 161.00 31.61 401 10050 1499784 109079064
Disease progression 139.85 31.61 142 10309 243892 110334956
Pneumocephalus 131.96 31.61 25 10426 473 110578375
Blood stem cell transplant failure 128.76 31.61 26 10425 692 110578156
Stem cell transplant 116.00 31.61 34 10417 4393 110574455
Progressive multifocal leukoencephalopathy 105.17 31.61 50 10401 24906 110553942
Diffuse large B-cell lymphoma recurrent 104.18 31.61 34 10417 6265 110572583
Venoocclusive disease 103.91 31.61 34 10417 6316 110572532
Malignant neoplasm progression 93.43 31.61 98 10353 174469 110404379
Thrombocytopenia 93.07 31.61 138 10313 348747 110230101
Neutropenic colitis 84.68 31.61 31 10420 8034 110570814
Therapy partial responder 83.88 31.61 49 10402 37012 110541836
Myositis 83.53 31.61 46 10405 31070 110547778
Febrile bone marrow aplasia 82.90 31.61 38 10413 17427 110561421
Cytomegalovirus infection reactivation 81.14 31.61 38 10413 18295 110560553
Pneumocystis jirovecii pneumonia 77.44 31.61 49 10402 42686 110536162
Aspergillus infection 71.88 31.61 39 10412 25577 110553271
Septic shock 67.93 31.61 79 10372 157449 110421399
Pneumonia adenoviral 67.77 31.61 15 10436 625 110578223
Disease recurrence 66.21 31.61 51 10400 60733 110518115
Cytomegalovirus infection 64.43 31.61 48 10403 54396 110524452
Acute graft versus host disease 64.20 31.61 29 10422 12852 110565996
Acute respiratory distress syndrome 63.17 31.61 47 10404 53151 110525697
Basal cell carcinoma 62.90 31.61 44 10407 45226 110533622
Gastroenteritis adenovirus 61.77 31.61 13 10438 426 110578422
Adenoviral hepatitis 60.94 31.61 15 10436 997 110577851
Aplasia 60.14 31.61 24 10427 7849 110570999
Bronchopulmonary aspergillosis 58.53 31.61 36 10415 29827 110549021
Arthralgia 58.26 31.61 4 10447 779628 109799220
Enterococcal infection 57.12 31.61 31 10420 20335 110558513
Metastatic lymphoma 56.84 31.61 13 10438 629 110578219
Cytopenia 55.73 31.61 35 10416 30081 110548767
Fatigue 55.32 31.61 23 10428 1215935 109362913
B-cell lymphoma recurrent 54.04 31.61 14 10437 1144 110577704
Human herpesvirus 6 infection 53.55 31.61 21 10430 6560 110572288
Product use in unapproved indication 52.03 31.61 124 10327 447253 110131595
Human herpesvirus 8 infection 51.80 31.61 15 10436 1856 110576992
Mantle cell lymphoma recurrent 50.78 31.61 13 10438 1013 110577835
JC virus infection 50.63 31.61 19 10432 5271 110573577
Neutropenic sepsis 50.14 31.61 33 10418 30713 110548135
Adenovirus infection 49.30 31.61 23 10428 10971 110567877
Colitis 48.64 31.61 54 10397 102269 110476579
Pain 48.60 31.61 15 10436 954940 109623908
Dizziness 48.26 31.61 5 10446 698188 109880660
Pancytopenia 47.51 31.61 77 10374 209536 110369312
Intracranial hypotension 46.34 31.61 11 10440 627 110578221
Metastases to muscle 46.20 31.61 10 10441 375 110578473
Pneumonia respiratory syncytial viral 46.11 31.61 15 10436 2734 110576114
Transformation to acute myeloid leukaemia 45.70 31.61 13 10438 1510 110577338
Metastases to retroperitoneum 45.15 31.61 10 10441 418 110578430
Neutropenia 43.70 31.61 104 10347 374516 110204332
Hemiplegia 43.47 31.61 27 10424 22755 110556093
Anal squamous cell carcinoma 43.18 31.61 11 10440 841 110578007
Brain abscess 42.71 31.61 18 10433 6756 110572092
Ureteric compression 42.47 31.61 9 10442 305 110578543
Pulmonary toxicity 41.57 31.61 24 10427 17722 110561126
Hemianopia 41.50 31.61 14 10437 2854 110575994
Malaise 41.21 31.61 7 10444 671812 109907036
Myelosuppression 40.12 31.61 47 10404 94293 110484555
Conjunctival haemorrhage 39.74 31.61 17 10434 6616 110572232
Hepatitis E 39.02 31.61 15 10436 4444 110574404
Cytokine release syndrome 38.50 31.61 40 10411 70266 110508582
Metastases to spleen 38.40 31.61 10 10441 834 110578014
Multiple organ dysfunction syndrome 37.49 31.61 58 10393 151652 110427196
Candida infection 37.06 31.61 33 10418 47976 110530872
Staphylococcal infection 36.89 31.61 39 10412 69905 110508943
Metastases to bone marrow 36.58 31.61 10 10441 1004 110577844
Bacteraemia 36.47 31.61 31 10420 42359 110536489
Lymphoma 36.21 31.61 23 10428 20148 110558700
Pleuroparenchymal fibroelastosis 35.65 31.61 8 10443 355 110578493
Cardiomyopathy acute 34.76 31.61 8 10443 398 110578450
Lymphadenopathy 34.38 31.61 36 10415 63799 110515049
Respiratory tract infection fungal 33.94 31.61 10 10441 1314 110577534
Lymphopenia 33.79 31.61 29 10422 40141 110538707
Enteritis 32.30 31.61 21 10430 19135 110559713
Hepatic angiosarcoma 31.84 31.61 6 10445 110 110578738

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
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:22333 alkylating agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35705 immunosuppressive agent
CHEBI has role CHEBI:67079 anti-inflammatory agent
MeSH PA D000477 Alkylating Agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018906 Antineoplastic Agents, Alkylating

Related Drugs by ATC class:

L01AD Nitrosoureas 7 drugs
fotemustinelomustinenimustineranimustinesemustinestreptozocinuracil mustard

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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

External reference:

IDSource
4020993 VUID
N0000148463 NUI
D00254 KEGG_DRUG
2105 RXNORM
C0007257 UMLSCUI
CHEBI:3423 CHEBI
I4E PDB_CHEM_ID
CHEMBL513 ChEMBL_ID
DB00262 DRUGBANK_ID
D002330 MESH_DESCRIPTOR_UI
2578 PUBCHEM_CID
6800 IUPHAR_LIGAND_ID
2959 INN_ID
U68WG3173Y UNII
251354 MMSL
399933 MMSL
4360 MMSL
d01342 MMSL
387281007 SNOMEDCT_US
51326002 SNOMEDCT_US
786790001 SNOMEDCT_US
4018136 VANDF
4020993 VANDF
002640 NDDF
U68WG3173Y INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Gliadel HUMAN PRESCRIPTION DRUG LABEL 1 24338-050 WAFER 7.70 mg INTRACAVITARY NDA 25 sections