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Details

Stereochemistry RACEMIC
Molecular Formula C15H19N3O5
Molecular Weight 321.3285
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBOQUONE

SMILES

COC(COC(N)=O)C1=C(N2CC2)C(=O)C(C)=C(N3CC3)C1=O

InChI

InChIKey=SHHKQEUPHAENFK-UHFFFAOYSA-N
InChI=1S/C15H19N3O5/c1-8-11(17-3-4-17)14(20)10(9(22-2)7-23-15(16)21)12(13(8)19)18-5-6-18/h9H,3-7H2,1-2H3,(H2,16,21)

HIDE SMILES / InChI

Molecular Formula C15H19N3O5
Molecular Weight 321.3285
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Carboquone (CQ) is an anticancer alkylating agent synthesized and developed by Arakawa et al. (Sankyo Co, Ltd.) in 1970, having chemical structure, 2,5-bis-(1-aziridinyl)-3-(2-carbamoyloxy-1-methoxyethyl)-6-methyl- 1,4- benzoquinone. The antitumor efficacies of CQ were reported as excellent, however, the side effects are considerably strong. Carboquone is used to treat various forms of cancer. It is indicated for the treatment of metastatic testicular tumors, metastatic ovarian tumors and advanced bladder cancer.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.009 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown
Primary
Unknown
Primary
Unknown
Primary
Carboquone
Primary
Carboquone
Primary
Carboquone

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Oral Chronic myeloid leukaemia Adult: Initial doses for remission induction: 1-2 mg daily. Maintenance: 0.25-0.75 mg every other day or twice wkly; adjust dose to maintain WBC count between 8000 and 15000/mm 3. Doses may vary depending on regimens. Oral Cancer chemotherapy Adult: 1-1.5 mg daily in 2-3 divided doses.
Route of Administration: Oral
In Vitro Use Guide
Treatment with 0.03 microM of CQ for 30 min inhibited the clonogenicity of HeLa cells by 41.5%.
Substance Class Chemical
Record UNII
1CB0HBT12C
Record Status Validated (UNII)
Record Version