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dacarbazine

Trade name: dtic-dome

Small moleculeapproved

Approved

May 27, 1975

Dacarbazine (DTIC), also known as imidazole carboxamide, is an antineoplastic agent, which is used in the treatment of metastatic malignant melanoma. In addition, this drug also is indicated for Hodgkin’s disease as a second-line therapy when used in combination with other effective agents. Dacarbazine works by methylating guanine at the O-6 and N-7 positions. Guanine is one of the four nucleotides that makes up DNA. The alkylated DNA strands stick together such that cell division becomes impossible. This affects cancer cells more than healthy cells because cancer cells divide faster. Dacarbazine is bioactivated in liver by demethylation to "MTIC" and then to diazomethane, which is an alkylating agent. Symptoms of anorexia, nausea, and vomiting are the most frequently noted of all toxic reactions. Over 90% of patients are affected with the initial few doses. — NCATS

Clinical trial activity

215 trials · 255 clinical orgs · 10 marketing orgs

Phase 1
26
Phase 2
181
Phase 3
73
Phase 4
5

Earliest trial started Jul 1, 1990 (NCT00002802)

Timeline

1970s

  1. May 27, 1975

    Bayer — Earliest FDA Approval

  2. May 27, 1975

    Bayer — NDA Organization

1980s

  1. Aug 28, 1986

    Abraxis — Marketing Organization

1990s

  1. Jan 1, 1990

    Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 1995

    Earliest Phase 2 Sponsor(trial)

  3. Aug 27, 1998

    Teva — Marketing Organization

  4. Aug 27, 1998

    Eu Yan Sang — Marketing Organization

  5. Aug 27, 1998

    Meitheal — Marketing Organization

  6. Aug 27, 1999

    Fresenius — Marketing Organization

2000s

  1. Jan 1, 2001

    Earliest Phase 1 Sponsor(trial)

  2. Jun 15, 2001

    West-Ward Pharmaceutical — Marketing Organization

  3. Jun 15, 2001

    Hikma — Marketing Organization

  4. Oct 18, 2001

    Hospira — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

  • DNAINHIBITOR

    DNA inhibitor

Approval history

  • approvedMay 27, 1975

Chemistry & pharmacology

Loading structure…

SMILES

CN(C)\N=N\C1=C(N=CN1)C(N)=O
Mol. weight
182.1832 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Parenteral
Availability
Prescription Only

Oral

No

Parenteral

Yes

Topical

No

Black box warning

Sources

Also known as

  • 4-(3,3-dimethyl-1-triazeno)imidazole-5-carboxamide
  • 4-(3,3-dimethyl-1-triazeno)imidazole-5-carboxamide
  • 4-(5)-(3,3-dimethyl-1-triazeno)imidazole-5(4)-carboxamide
  • 4-(5)-(3,3-dimethyl-1-triazeno)imidazole-5(4)-carboxamide
  • 4-(dimethyltriazeno)imidazole-5-carboxamide
  • 4-(dimethyltriazeno)imidazole-5-carboxamide
  • 4-(dimethyltriazeno)imidazole-5-carboxamide
  • 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide
  • 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide
  • 5-(3,3-dimethyltriazeno)imidazole-4-carboxamide
  • 5-(3,3-dimethyltriazeno)imidazole-4-carboxamide
  • 5-(dimethyltriazeno)imidazole-4-carboxamide
  • 5-(dimethyltriazeno)imidazole-4-carboxamide
  • 5-(dimethyltriazeno)imidazole-4-carboxamide
  • biocarbazine
  • biocarbazine
  • biocarbazine
  • dacarbacine
  • dacarbazin
  • dacarbazin
  • dacarbazina
  • dacarbazina
  • dacarbazina
  • dacarbazine
  • dacarbazine
  • dacarbazine
  • dacarbazine
  • dacarbazine
  • dacarbazine
  • dacarbazine
  • dacarbazine
  • dacarbazine
  • dacarbazinum
  • dacarbazinum
  • darcabazine
  • decarbazine
  • decarbazine
  • deticene
  • deticene
  • deticene
  • deticene
  • deticene
  • deticene
  • deticene
  • dic
  • dic
  • dic
  • dic
  • dtci
  • dtci
  • dtic
  • dtic
  • dtic
  • dtic-dome
  • dtic-dome
  • dtic-dome
  • dtic-dome
  • icdmt
  • icdmt
  • sentoclone

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07275216Phase 2Jul 1, 2026City of Hope National Medical Center, National Cancer Institute (NCI)
NCT07310784Phase 2Dec 16, 2025Government of China
NCT07002216Phase 2Jul 15, 2025Pfizer, University of Miami
NCT06745076Phase 2Jun 1, 2025University of Washington
NCT06835049Phase 2May 15, 2025Swiss Cancer Institute, University of Bern
NCT06984146Phase 2Apr 15, 2025Government of Russia
NCT06743126Phase 3Dec 31, 2024immatics Biotechnologies GmbH
NCT06703398Phase 2Dec 20, 2024Government of China
NCT06624644Phase 2/Phase 3 (Phase 3)Nov 30, 2024Linnaeus Therapeutics, Inc., Merck
NCT06848569Phase 2Oct 23, 2024Sun Yat-Sen University
NCT06563245Phase 2/Phase 3 (Phase 3)Sep 25, 2024Anhui Medical University, Central South University, Children's Cancer Group, China, Hebei University, Huazhong University of Science and Technology, Jiao Tong University, Shandong University, Sichuan University, Sun Yat-Sen University, Tianjin Medical University, Tongji University, Zhengzhou University
NCT06831370Phase 4Aug 28, 2024Takeda
NCT06346067Phase 3Apr 29, 2024Erasca, Inc.
NCT06377566Phase 2Apr 17, 2024Memorial Sloan-Kettering Cancer Center, Seattle Genetics
NCT06164275Phase 2Dec 31, 2023National Cancer Institute (NCI), Northwestern University
NCT05922904Phase 2Dec 14, 2023Merck, Seattle Genetics, University of Texas at Houston
NCT05987332Phase 2/Phase 3 (Phase 3)Oct 31, 2023IDEAYA Biosciences
NCT06008106Phase 3Sep 22, 2023Kechow Pharma
NCT05949931Phase 2Aug 31, 2023Sun Yat-Sen University
NCT05675410Phase 3May 11, 2023National Cancer Institute (NCI), State University of New York, Buffalo
Showing 20 of 215 trials
Page 1 / 11

Organizations

Research & Development (255)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Cancer Institute (NCI)Government301041995
Seattle GeneticsFor profit13352010
Bristol-Myers SquibbFor profit12732006
University of Texas at HoustonAcademic/Hospital11831995
University of CologneAcademic/Hospital101031998
MerckFor profit8422004
Eastern Cooperative Oncology GroupAcademic/Hospital7221994
European Organisation for Research and Treatment of CancerAcademic/Hospital7621995
Cornell UniversityAcademic/Hospital6432008
AstraZenecaFor profit5532006
Fondazione Italiana Diabete OnlusAcademic/Hospital5422006
Millennium PharmaceuticalsFor profit5232010
Southwest Oncology GroupAcademic/Hospital5321997
Stanford UniversityAcademic/Hospital5131999
The Lymphoma Study AssociationAcademic/Hospital5021998
Canadian Cancer Trials GroupAcademic/Hospital4221994
City of Hope National Medical CenterAcademic/Hospital4232013
Harvard UniversityAcademic/Hospital4222000
Justus Liebig University GiessenAcademic/Hospital4332002
Northwestern UniversityAcademic/Hospital4321994
255 organizations
Page 1 / 13

Marketing (11)

OrganizationOrg typeRelationshipDate
AbraxisFor profitMKTGAug 28, 1986
Athenex, Inc.For profitMKTG—
BayerFor profitNDAMay 27, 1975
Eu Yan SangFor profitMKTGAug 27, 1998
FreseniusFor profitMKTGAug 27, 1999
HikmaFor profitSYNJun 15, 2001
HikmaFor profitMKTGJun 15, 2001
HospiraFor profitMKTGOct 18, 2001
MeithealFor profitMKTGAug 27, 1998
TevaFor profitMKTGAug 27, 1998
West-Ward PharmaceuticalFor profitMKTGJun 15, 2001