dacarbazine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	773	4342-03-4

Description:

Molecule	Description
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

Molecule

Description

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:

None

ADMET properties:

Property	Value	Reference
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

Approvals:

Date	Agency	Company	Orphan
May 27, 1975	FDA	BAYER HLTHCARE

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
Febrile neutropenia	211.03	27.28	130	5399	118319	63365174
Neutropenia	165.11	27.28	130	5399	174875	63308618
Disease progression	148.69	27.28	106	5423	122652	63360841
Pulmonary toxicity	116.29	27.28	40	5489	9415	63474078
Second primary malignancy	76.35	27.28	28	5501	7925	63475568
Tissue infiltration	69.26	27.28	15	5514	614	63482879
Malignant neoplasm progression	68.69	27.28	57	5472	82064	63401429
Basal ganglion degeneration	68.42	27.28	14	5515	434	63483059
Uterine enlargement	58.80	27.28	15	5514	1253	63482240
Pneumocystis jirovecii pneumonia	56.00	27.28	28	5501	16886	63466607
Dysaesthesia	55.26	27.28	19	5510	4459	63479034
Inguinal hernia	51.98	27.28	15	5514	1992	63481501
Anaesthesia	51.43	27.28	11	5518	424	63483069
Psychogenic seizure	49.92	27.28	14	5515	1678	63481815
Myelodysplastic syndrome	47.54	27.28	25	5504	16729	63466764
Cardiotoxicity	46.85	27.28	20	5509	8418	63475075
Exposure during pregnancy	46.06	27.28	62	5467	155485	63328008
Neurological decompensation	43.79	27.28	14	5515	2624	63480869
Interstitial lung disease	43.67	27.28	39	5490	61869	63421624
Hypochromic anaemia	43.63	27.28	13	5516	1929	63481564
Monoplegia	41.13	27.28	14	5515	3187	63480306
Product use in unapproved indication	39.36	27.28	62	5467	179018	63304475
Pleuroparenchymal fibroelastosis	38.80	27.28	7	5522	109	63483384
Acute myeloid leukaemia	38.71	27.28	22	5507	17125	63466368
Hyperpyrexia	35.64	27.28	13	5516	3619	63479874
Pyrexia	35.16	27.28	105	5424	470373	63013120
Premature menopause	33.92	27.28	9	5520	877	63482616
Klebsiella infection	33.82	27.28	16	5513	8550	63474943
Sarcoidosis	33.43	27.28	15	5514	7107	63476386
Febrile bone marrow aplasia	33.02	27.28	15	5514	7310	63476183
Pancytopenia	32.34	27.28	41	5488	96892	63386601
Intervertebral disc disorder	32.00	27.28	13	5516	4830	63478663
Candida infection	30.84	27.28	23	5506	28328	63455165
Foetal exposure during pregnancy	30.53	27.28	24	5505	31938	63451555
Meningitis streptococcal	30.52	27.28	6	5523	151	63483342
Premature baby	29.93	27.28	20	5509	20715	63462778
Anaemia	29.39	27.28	73	5456	293357	63190136
Hyperventilation	29.08	27.28	13	5516	6103	63477390
Neuropathy peripheral	28.69	27.28	42	5487	113625	63369868
Off label use	28.55	27.28	125	5404	674337	62809156
Abdominal tenderness	28.45	27.28	14	5515	8152	63475341
Renal cyst	28.16	27.28	15	5514	10287	63473206
Infusion site joint movement impairment	27.85	27.28	4	5525	12	63483481

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
Second primary malignancy	195.52	25.05	66	5639	7820	34943406
Febrile neutropenia	193.18	25.05	167	5538	136682	34814544
Acute myeloid leukaemia	141.74	25.05	66	5639	18204	34933022
Malignant neoplasm progression	110.99	25.05	101	5604	87945	34863281
Neutropenia	106.22	25.05	129	5576	156649	34794577
Cardiotoxicity	93.31	25.05	35	5670	5613	34945613
Disease progression	81.44	25.05	94	5611	107983	34843243
Pulmonary toxicity	79.89	25.05	32	5673	6115	34945111
Endocarditis noninfective	75.89	25.05	14	5691	126	34951100
Neutrophil count decreased	70.97	25.05	62	5643	51042	34900184
Chronic myeloid leukaemia	60.58	25.05	20	5685	2204	34949022
Myositis	59.26	25.05	32	5673	12038	34939188
Interstitial lung disease	54.57	25.05	60	5645	65222	34886004
Product use in unapproved indication	50.92	25.05	78	5627	117421	34833805
Pneumocystis jirovecii pneumonia	47.12	25.05	33	5672	19677	34931549
Off label use	44.16	25.05	159	5546	419365	34531861
Autoimmune neutropenia	43.90	25.05	10	5695	271	34950955
Pneumonitis	42.82	25.05	39	5666	33839	34917387
Cardiac dysfunction	36.83	25.05	14	5691	2324	34948902
Acute lymphocytic leukaemia	36.70	25.05	15	5690	3014	34948212
Ichthyosis	34.72	25.05	7	5698	104	34951122
Pneumonia salmonella	33.04	25.05	6	5699	49	34951177
Asthenospermia	31.60	25.05	6	5699	64	34951162
Guillain-Barre syndrome	29.48	25.05	16	5689	6071	34945155
Pyrexia	28.98	25.05	119	5586	332894	34618332
Spindle cell sarcoma	27.67	25.05	6	5699	129	34951097
Oropharyngeal squamous cell carcinoma	25.17	25.05	6	5699	199	34951027
Peripheral nerve injury	25.11	25.05	6	5699	201	34951025

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
Febrile neutropenia	337.81	22.05	260	9931	230739	79503458
Second primary malignancy	290.20	22.05	97	10094	14253	79719944
Neutropenia	260.51	22.05	246	9945	287464	79446733
Disease progression	194.57	22.05	172	10019	184190	79550007
Pulmonary toxicity	186.73	22.05	68	10123	12846	79721351
Acute myeloid leukaemia	183.28	22.05	86	10105	30799	79703398
Malignant neoplasm progression	178.67	22.05	144	10047	135846	79598351
Cardiotoxicity	101.15	22.05	43	10148	12196	79722001
Pneumocystis jirovecii pneumonia	93.95	22.05	56	10135	32452	79701745
Product use in unapproved indication	90.43	22.05	134	10057	250225	79483972
Neutrophil count decreased	89.72	22.05	83	10108	93876	79640321
Interstitial lung disease	89.67	22.05	90	10101	112510	79621687
Myelodysplastic syndrome	79.33	22.05	49	10142	30252	79703945
Endocarditis noninfective	72.30	22.05	14	10177	217	79733980
Myelitis	68.16	22.05	21	10170	2370	79731827
Chronic myeloid leukaemia	59.36	22.05	21	10170	3643	79730554
Pleuroparenchymal fibroelastosis	58.54	22.05	11	10180	144	79734053
Off label use	55.08	22.05	245	9946	906970	78827227
Pneumonitis	54.67	22.05	52	10139	60808	79673389
Myositis	52.73	22.05	32	10159	19136	79715061
Basal ganglion degeneration	52.21	22.05	12	10179	436	79733761
Tissue infiltration	51.99	22.05	13	10178	678	79733519
Pyrexia	50.29	22.05	195	9996	678514	79055683
Uterine enlargement	48.47	22.05	13	10178	895	79733302
Candida infection	46.97	22.05	39	10152	38175	79696022
Acute lymphocytic leukaemia	42.85	22.05	18	10173	4951	79729246
Neuropathy peripheral	41.68	22.05	69	10122	141236	79592961
Anaesthesia	40.08	22.05	10	10181	517	79733680
Dysaesthesia	40.03	22.05	18	10173	5830	79728367
Sarcoidosis	39.74	22.05	20	10171	8315	79725882
Psychogenic seizure	38.79	22.05	13	10178	1918	79732279
Autoimmune neutropenia	38.77	22.05	10	10181	591	79733606
Therapy partial responder	37.75	22.05	25	10166	17372	79716825
Intestinal perforation	37.71	22.05	25	10166	17401	79716796
Platelet toxicity	37.48	22.05	5	10186	3	79734194
Pancytopenia	37.40	22.05	72	10119	165673	79568524
Asthenospermia	35.20	22.05	6	10185	43	79734154
Neoplasm progression	35.15	22.05	38	10153	51644	79682553
Lung disorder	34.73	22.05	47	10144	80510	79653687
Respiratory failure	34.18	22.05	73	10118	180838	79553359
Tooth malformation	33.96	22.05	7	10184	151	79734046
Ichthyosis	33.74	22.05	7	10184	156	79734041
Pneumonia salmonella	33.51	22.05	6	10185	59	79734138
Myelosuppression	33.49	22.05	33	10158	40263	79693934
Ileus	32.73	22.05	27	10164	26184	79708013
Cytopenia	31.92	22.05	24	10167	20359	79713838
Hodgkin's disease recurrent	31.59	22.05	5	10186	21	79734176
Acute promyelocytic leukaemia	29.80	22.05	10	10181	1481	79732716
Anaemia	29.75	22.05	124	10067	444891	79289306
Monoplegia	29.68	22.05	13	10178	3958	79730239
White blood cell count decreased	28.92	22.05	70	10121	188218	79545979
Left ventricular dysfunction	28.57	22.05	22	10169	19339	79714858
Guillain-Barre syndrome	27.34	22.05	16	10175	8949	79725248
Sepsis	27.29	22.05	86	10105	269342	79464855
Hypochromic anaemia	27.23	22.05	11	10180	2740	79731457
Metastatic malignant melanoma	26.81	22.05	11	10180	2852	79731345
Infusion site joint movement impairment	26.32	22.05	4	10187	12	79734185
Neurological decompensation	26.20	22.05	13	10178	5240	79728957
Spindle cell sarcoma	25.84	22.05	6	10185	228	79733969
Lymphopenia	25.34	22.05	25	10166	30532	79703665
Oropharyngeal squamous cell carcinoma	25.08	22.05	6	10185	260	79733937
Abdominal tenderness	24.88	22.05	16	10175	10578	79723619
Hypothyroidism	24.79	22.05	32	10159	52360	79681837
Renal cyst	24.53	22.05	18	10173	14714	79719483
Thrombocytopenia	24.45	22.05	82	10109	265177	79469020
Polyneuropathy	24.31	22.05	22	10169	24129	79710068
Intervertebral disc disorder	24.24	22.05	12	10179	4813	79729384
Haemophagocytic lymphohistiocytosis	24.19	22.05	21	10170	21816	79712381
Rash	24.19	22.05	23	10168	578335	79155862
Joint swelling	24.06	22.05	4	10187	288642	79445555
Pain	24.02	22.05	33	10158	703769	79030428
Hodgkin's disease nodular sclerosis	23.94	22.05	4	10187	25	79734172
Inguinal hernia	23.62	22.05	13	10178	6475	79727722
Pancreatic neuroendocrine tumour metastatic	23.52	22.05	5	10186	126	79734071
Invasive lobular breast carcinoma	23.50	22.05	7	10184	704	79733493
Infusion site ulcer	23.19	22.05	4	10187	31	79734166
Weight increased	22.77	22.05	4	10187	277382	79456815
Infusion site hypoaesthesia	22.66	22.05	4	10187	36	79734161
Tumour lysis syndrome	22.53	22.05	21	10170	23918	79710279

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	L01AX04	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ALKYLATING AGENTS Other alkylating agents
FDA MoA	N0000000236	Alkylating Activity
FDA EPC	N0000175558	Alkylating Drug
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:50266	Prodrugs
CHEBI has role	CHEBI:50903	carcinogen
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
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Matrix metalloproteinase-9	Enzyme	P14780	MMP9_HUMAN		IC50	6.26		DRUG MATRIX
DNA polymerase alpha subunit B	Enzyme	Q14181	DPOA2_HUMAN					WOMBAT-PK

External reference:

ID	Source
4018386	VUID
N0000146713	NUI
D00288	KEGG_DRUG
3098	RXNORM
4018386	VANDF
C0010927	UMLSCUI
CHEBI:4305	CHEBI
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

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Dacarbazine	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9245	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	10 mg	INTRAVENOUS	ANDA	16 sections
Dacarbazine	HUMAN PRESCRIPTION DRUG LABEL	1	0703-5075	INJECTION, POWDER, FOR SOLUTION	200 mg	INTRAVENOUS	ANDA	17 sections
Dacarbazine	HUMAN PRESCRIPTION DRUG LABEL	1	0703-5075	INJECTION, POWDER, FOR SOLUTION	200 mg	INTRAVENOUS	ANDA	17 sections
Dacarbazine	HUMAN PRESCRIPTION DRUG LABEL	1	0703-5075	INJECTION, POWDER, FOR SOLUTION	200 mg	INTRAVENOUS	ANDA	17 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	63323-127	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	63323-128	INJECTION, POWDER, FOR SOLUTION	10 mg	INTRAVENOUS	ANDA	14 sections