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

Stem definitionDrug idCAS RN
773 4342-03-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • deticene
  • dacarbazine
An antineoplastic agent. It has significant activity against melanomas. (from Martindale, The Extra Pharmacopoeia, 31st ed, p564)
  • Molecular weight: 182.19
  • Formula: C6H10N6O
  • CLOGP: 0.47
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 99.73
  • ALOGS: -2.12
  • ROTB: 3
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
43.30 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 4.20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 39 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 24.70 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6.20 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ALK,AURKA,AXL,BRAF,CAMK2B,CAMK2D,CDK1,CDK5,CDK9,CSF1R,DDR1,DYRK1B,EIF2AK3,ERBB2,FLT3,GRK2,GSK3B,IRAK1,ITK,JAK1,JAK2,KIT,MAP2K6,MAP3K1,MAP3K10,MAP3K11,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAPK7,MAPK9,MARK4,MTOR,NTRK1,NTRK2,PDK1,PDK2,PIK3CG,PIM2,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1,ULK2 53
kinase-selectivity-class ACVR2A,ACVR2B,AXL,BRAF,CAMK2D,CDK16,CDK9,CLK2,CLK4,DYRK1B,EIF2AK3,GRK2,GSK3B,JAK2,MAP2K3,MAP2K6,MAP3K14,MAP3K21,MAPK7,MARK4,PRKDC,SIK2,STK33,SYK,TEK,TTK,ULK1 27
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
May 27, 1975 FDA BAYER HLTHCARE

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
Febrile neutropenia 397.18 28.19 209 6864 158140 90463234
Neutropenia 249.08 28.19 176 6897 224728 90396646
Disease progression 190.56 28.19 130 6943 156485 90464889
Pulmonary toxicity 124.29 28.19 43 7030 11488 90609886
Neuropathy peripheral 117.19 28.19 92 6981 136878 90484496
Second primary malignancy 79.23 28.19 30 7043 10348 90611026
Interstitial lung disease 77.82 28.19 57 7016 76348 90545026
Malignant neoplasm progression 77.03 28.19 65 7008 106805 90514569
Pneumocystis jirovecii pneumonia 63.92 28.19 32 7041 21584 90599790
Basal ganglion degeneration 60.01 28.19 12 7061 370 90621004
Myelosuppression 56.87 28.19 41 7032 53550 90567824
Tissue infiltration 55.39 28.19 13 7060 857 90620517
Off label use 54.84 28.19 199 6874 1102053 89519321
Therapy partial responder 54.69 28.19 29 7044 22014 90599360
Dysaesthesia 54.31 28.19 19 7054 5236 90616138
Febrile bone marrow aplasia 52.83 28.19 22 7051 9716 90611658
Anaesthesia 51.92 28.19 11 7062 453 90620921
Pancytopenia 50.02 28.19 54 7019 120209 90501165
Premature menopause 49.92 28.19 13 7060 1316 90620058
Uterine enlargement 49.74 28.19 13 7060 1335 90620039
Cardiotoxicity 49.52 28.19 22 7051 11367 90610007
Anaemia 48.04 28.19 93 6980 352709 90268665
Acute polyneuropathy 46.32 28.19 10 7063 451 90620923
Pyrexia 45.09 28.19 133 6940 660352 89961022
Myelodysplastic syndrome 44.91 28.19 25 7048 20878 90600496
Psychogenic seizure 44.56 28.19 13 7060 2003 90619371
Inguinal hernia 44.04 28.19 13 7060 2085 90619289
Posterior reversible encephalopathy syndrome 43.36 28.19 25 7048 22314 90599060
Exposure during pregnancy 41.54 28.19 70 7003 238340 90383034
Neutrophil count decreased 40.54 28.19 38 7035 71494 90549880
Hypochromic anaemia 39.30 28.19 12 7061 2159 90619215
Neurological decompensation 37.50 28.19 13 7060 3488 90617886
Thrombocytopenia 37.31 28.19 62 7011 208663 90412711
Acute myeloid leukaemia 37.16 28.19 22 7051 20618 90600756
Monoplegia 36.88 28.19 13 7060 3661 90617713
Pleuroparenchymal fibroelastosis 35.42 28.19 7 7066 203 90621171
Bone pain 35.26 28.19 33 7040 61950 90559424
Neoplasm progression 33.97 28.19 28 7045 44458 90576916
Candida infection 33.73 28.19 25 7048 34032 90587342
Colitis 33.71 28.19 34 7039 69908 90551466
Sarcoidosis 32.14 28.19 16 7057 10657 90610717
Intervertebral disc disorder 31.87 28.19 13 7060 5447 90615927
Meningitis streptococcal 31.65 28.19 6 7067 139 90621235
Leukopenia 31.40 28.19 39 7034 100671 90520703
Polyneuropathy 30.65 28.19 19 7054 19322 90602052
Bacteraemia 30.60 28.19 20 7053 22280 90599094
Hyperpyrexia 30.08 28.19 12 7061 4749 90616625
Cytopenia 29.85 28.19 18 7055 17431 90603943
Respiratory failure 29.40 28.19 41 7032 118377 90502997
Lymphadenopathy 29.21 28.19 26 7047 45749 90575625
Haemophagocytic lymphohistiocytosis 29.20 28.19 17 7056 15442 90605932
Genital ulceration 28.56 28.19 8 7065 1065 90620309
Premature baby 28.47 28.19 20 7053 25057 90596317
Infusion site joint movement impairment 28.29 28.19 4 7069 12 90621362

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
Febrile neutropenia 281.68 23.74 244 7276 185459 42428356
Second primary malignancy 226.85 23.74 79 7441 9496 42604319
Acute myeloid leukaemia 150.49 23.74 75 7445 22181 42591634
Neutropenia 150.41 23.74 180 7340 199251 42414564
Malignant neoplasm progression 111.04 23.74 115 7405 108285 42505530
Disease progression 106.97 23.74 129 7391 143527 42470288
Pulmonary toxicity 88.99 23.74 39 7481 8616 42605199
Cardiotoxicity 87.91 23.74 37 7483 7408 42606407
Endocarditis noninfective 72.59 23.74 14 7506 150 42613665
Myositis 71.70 23.74 40 7480 14826 42598989
Neutrophil count decreased 69.77 23.74 70 7450 63345 42550470
Off label use 64.07 23.74 251 7269 638084 41975731
Chronic myeloid leukaemia 60.66 23.74 21 7499 2471 42611344
Neuropathy peripheral 59.20 23.74 81 7439 101772 42512043
Interstitial lung disease 48.00 23.74 64 7456 78398 42535417
Neoplasm progression 47.45 23.74 40 7480 28960 42584855
Product use in unapproved indication 45.11 23.74 100 7420 184356 42429459
Pneumonitis 43.93 23.74 45 7475 41673 42572142
Pneumocystis jirovecii pneumonia 43.83 23.74 36 7484 25145 42588670
Therapy partial responder 42.11 23.74 32 7488 19989 42593826
Autoimmune neutropenia 40.72 23.74 10 7510 348 42613467
Peripheral sensory neuropathy 40.67 23.74 23 7497 8739 42605076
Asthenospermia 37.01 23.74 7 7513 67 42613748
Peripheral nerve injury 36.54 23.74 9 7511 317 42613498
Pyrexia 35.31 23.74 150 7370 393892 42219923
Vasogenic cerebral oedema 34.26 23.74 11 7509 1025 42612790
Cardiac dysfunction 33.90 23.74 15 7505 3384 42610431
Acute lymphocytic leukaemia 33.77 23.74 15 7505 3416 42610399
Ichthyosis 31.76 23.74 7 7513 150 42613665
Myelosuppression 31.08 23.74 37 7483 40424 42573391
Pneumonia salmonella 30.48 23.74 6 7514 72 42613743
Guillain-Barre syndrome 28.25 23.74 17 7503 7246 42606569
Nodular lymphocyte predominant Hodgkin lymphoma 26.91 23.74 4 7516 6 42613809
Cytopenia 26.30 23.74 23 7497 17474 42596341
Spindle cell sarcoma 26.19 23.74 6 7514 154 42613661
Leukopenia 25.99 23.74 47 7473 74699 42539116
Meningoencephalitis amoebic 23.89 23.74 6 7514 229 42613586

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
Febrile neutropenia 550.58 22.79 387 13001 316380 110259531
Neutropenia 359.38 22.79 323 13065 374297 110201614
Second primary malignancy 327.51 22.79 111 13277 17957 110557954
Disease progression 256.67 22.79 222 13166 243812 110332099
Pulmonary toxicity 204.54 22.79 78 13310 17668 110558243
Acute myeloid leukaemia 197.28 22.79 95 13293 38015 110537896
Malignant neoplasm progression 183.72 22.79 159 13229 174408 110401503
Neuropathy peripheral 154.58 22.79 146 13242 179131 110396780
Pneumocystis jirovecii pneumonia 122.93 22.79 72 13316 42663 110533248
Interstitial lung disease 115.34 22.79 111 13277 139223 110436688
Neutrophil count decreased 110.92 22.79 102 13286 120839 110455072
Cardiotoxicity 102.48 22.79 47 13341 16834 110559077
Off label use 100.88 22.79 402 12986 1499783 109076128
Myelosuppression 85.38 22.79 79 13309 94261 110481650
Product use in unapproved indication 75.69 22.79 167 13221 447210 110128701
Neoplasm progression 72.23 22.79 61 13327 64534 110511377
Myelodysplastic syndrome 72.20 22.79 49 13339 37435 110538476
Endocarditis noninfective 69.18 22.79 14 13374 291 110575620
Pneumonitis 67.14 22.79 63 13325 76468 110499443
Pyrexia 64.27 22.79 246 13142 898019 109677892
Myelitis 63.17 22.79 21 13367 3192 110572719
Chronic myeloid leukaemia 61.04 22.79 22 13366 4251 110571660
Therapy partial responder 61.00 22.79 44 13344 37017 110538894
Myositis 60.70 22.79 41 13347 31075 110544836
Anaemia 59.77 22.79 173 13215 546913 110028998
Cytopenia 57.12 22.79 39 13349 30077 110545834
Pancytopenia 53.34 22.79 93 13295 209520 110366391
Basal ganglion degeneration 53.18 22.79 12 13376 424 110575487
Thrombocytopenia 53.12 22.79 125 13263 348760 110227151
Candida infection 52.97 22.79 45 13343 47964 110527947
White blood cell count decreased 51.02 22.79 96 13292 229294 110346617
Pleuroparenchymal fibroelastosis 49.80 22.79 11 13377 352 110575559
Haematotoxicity 48.99 22.79 31 13357 21051 110554860
Uterine enlargement 48.12 22.79 13 13375 972 110574939
Tissue infiltration 47.38 22.79 13 13375 1030 110574881
Respiratory failure 46.50 22.79 89 13299 215243 110360668
Ileus 44.98 22.79 34 13354 30695 110545216
Anaesthesia 44.23 22.79 11 13377 593 110575318
Sepsis 43.15 22.79 111 13277 327235 110248676
Asthenospermia 41.97 22.79 7 13381 46 110575865
Acute polyneuropathy 41.60 22.79 11 13377 757 110575154
Dysaesthesia 41.35 22.79 19 13369 6828 110569083
Acute lymphocytic leukaemia 41.21 22.79 18 13370 5747 110570164
Joint swelling 39.32 22.79 4 13384 442841 110133070
Posterior reversible encephalopathy syndrome 37.89 22.79 32 13356 33829 110542082
Autoimmune neutropenia 37.64 22.79 10 13378 701 110575210
Intestinal perforation 37.08 22.79 26 13362 20918 110554993
Psychogenic seizure 36.90 22.79 13 13375 2351 110573560
Disease recurrence 36.83 22.79 41 13347 60743 110515168
Sarcoidosis 35.64 22.79 21 13367 12558 110563353
Polyneuropathy 35.30 22.79 30 13358 31982 110543929
Tooth malformation 34.34 22.79 7 13381 151 110575760
Febrile bone marrow aplasia 34.03 22.79 23 13365 17442 110558469
Mucosal inflammation 33.13 22.79 49 13339 96092 110479819
Platelet toxicity 32.92 22.79 5 13383 16 110575895
Peripheral sensory neuropathy 32.58 22.79 22 13366 16658 110559253
Metastatic malignant melanoma 32.27 22.79 13 13375 3396 110572515
Ichthyosis 32.22 22.79 7 13381 207 110575704
Colitis 32.21 22.79 50 13338 102273 110473638
Pneumonia salmonella 32.01 22.79 6 13382 82 110575829
Leukopenia 31.49 22.79 61 13327 148730 110427181
Guillain-Barre syndrome 30.61 22.79 18 13370 10726 110565185
Pain 30.28 22.79 43 13345 954912 109620999
Left ventricular dysfunction 30.05 22.79 24 13364 23469 110552442
Hypochromic anaemia 29.59 22.79 12 13376 3189 110572722
Meningitis aseptic 29.34 22.79 17 13371 9853 110566058
Headache 28.70 22.79 39 13349 882338 109693573
Peripheral nerve injury 28.68 22.79 9 13379 1139 110574772
Weight increased 28.08 22.79 8 13380 419636 110156275
Acute promyelocytic leukaemia 27.98 22.79 10 13378 1886 110574025
Pruritus 27.96 22.79 18 13370 581542 109994369
Monoplegia 27.71 22.79 13 13375 4896 110571015
Nodular lymphocyte predominant Hodgkin lymphoma 27.36 22.79 4 13384 9 110575902
Rash 26.98 22.79 36 13352 820928 109754983
Swelling 26.85 22.79 5 13383 351036 110224875
Progressive multifocal leukoencephalopathy 26.72 22.79 23 13365 24933 110550978
Infusion site joint movement impairment 26.53 22.79 4 13384 12 110575899
Vanishing bile duct syndrome 26.31 22.79 11 13377 3157 110572754
Intervertebral disc disorder 26.28 22.79 13 13375 5499 110570412
Anxiety 26.21 22.79 5 13383 345073 110230838
Meningoencephalitis amoebic 25.91 22.79 6 13382 238 110575673
Nasopharyngitis 25.51 22.79 8 13380 394353 110181558
Spindle cell sarcoma 25.44 22.79 6 13382 258 110575653
Acanthamoeba infection 24.79 22.79 7 13381 616 110575295
Infusion related reaction 24.18 22.79 8 13380 381154 110194757
Hodgkin's disease nodular sclerosis 24.16 22.79 4 13384 25 110575886
Infusion site ulcer 24.16 22.79 4 13384 25 110575886
Haemophagocytic lymphohistiocytosis 23.94 22.79 24 13364 31535 110544376
Oropharyngeal squamous cell carcinoma 23.87 22.79 6 13382 338 110575573
Arthralgia 23.81 22.79 36 13352 779596 109796315
Bone pain 23.60 22.79 34 13354 65099 110510812
Neurological decompensation 23.55 22.79 13 13375 6870 110569041
Muscle spasms 23.46 22.79 3 13385 278154 110297757
Urticaria 23.42 22.79 5 13383 318852 110257059
Abdominal tenderness 23.30 22.79 16 13372 12441 110563470
Hepatotoxicity 22.83 22.79 33 13355 63367 110512544

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L01AX04 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ALKYLATING AGENTS
Other alkylating agents
FDA MoA N0000000236 Alkylating Activity
FDA EPC N0000175558 Alkylating Drug
MeSH PA D000477 Alkylating Agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018906 Antineoplastic Agents, Alkylating
CHEBI has role CHEBI:22333 alkylating agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:50903 carcinogenic agent

Related Drugs by ATC class:

L01AX Other alkylating agents 3 drugs
mitobronitolpipobromantemozolomide

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Hodgkin's disease indication 118599009
Metastatic malignant melanoma indication 443493003
Pancreatic Neuroendocrine Tumor off-label use 717919005
Hepatic vein thrombosis contraindication 38739001 DOID:11512
Leukopenia contraindication 84828003 DOID:615
Hepatic necrosis contraindication 87248009
Kidney disease contraindication 90708001 DOID:557
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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.06 acidic
pKa2 11.73 acidic
pKa3 4.18 Basic

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
Matrix metalloproteinase-9 Enzyme IC50 6.26 DRUG MATRIX
DNA polymerase alpha subunit B Enzyme WOMBAT-PK

External reference:

IDSource
4018386 VUID
N0000146713 NUI
D00288 KEGG_DRUG
3098 RXNORM
C0010927 UMLSCUI
CHEBI:4305 CHEBI
A1E2W PDB_CHEM_ID
CHEMBL476 ChEMBL_ID
DB00851 DRUGBANK_ID
D003606 MESH_DESCRIPTOR_UI
135398738 PUBCHEM_CID
3232 INN_ID
9075 IUPHAR_LIGAND_ID
7GR28W0FJI UNII
31748 MMSL
4528 MMSL
d00202 MMSL
002671 NDDF
387441003 SNOMEDCT_US
77750008 SNOMEDCT_US
4018386 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Dacarbazine HUMAN PRESCRIPTION DRUG LABEL 1 0143-9245 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 200 mg INTRAVENOUS ANDA 16 sections
Dacarbazine HUMAN PRESCRIPTION DRUG LABEL 1 63323-127 INJECTION, POWDER, FOR SOLUTION 10 mg INTRAVENOUS ANDA 14 sections
Dacarbazine HUMAN PRESCRIPTION DRUG LABEL 1 63323-128 INJECTION, POWDER, FOR SOLUTION 10 mg INTRAVENOUS ANDA 14 sections
Dacarbazine HUMAN PRESCRIPTION DRUG LABEL 1 71288-174 INJECTION, POWDER, FOR SOLUTION 200 mg INTRAVENOUS ANDA 17 sections