CARMOFUR

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16FN3O3
Molecular Weight	257.2614
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O

InChI

InChIKey=AOCCBINRVIKJHY-UHFFFAOYSA-N

InChI=1S/C11H16FN3O3/c1-2-3-4-5-6-13-10(17)15-7-8(12)9(16)14-11(15)18/h7H,2-6H2,1H3,(H,13,17)(H,14,16,18)

HIDE SMILES / InChI

Molecular Formula	C11H16FN3O3
Molecular Weight	257.2614
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Carmofur, also known as 5-fluoro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide and as 1-hexylcarbamoyl-5-fluorouracil, is a pyrimidine analogue which acts as an antineoplastic agent through inhibition of thymidylate synthase. It has been used in the treatment of breast and colorectal cancer. Carmofur is approved in Japan for the treatment of cancer.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acid ceramidase 1	Inhibitor 8,297		29.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pancreatic cancer 97	Primary	Phase II 1,132	Unknown
Gastric cancer 53	Primary	Approved 8,429	Carmofur
Breast cancer 434	Primary	Approved 8,429	Carmofur

AUC

Value	Dose	Co-administered	Analyte	Population
6.51 μg × h/mL	100 mg single, oral		CARMOFUR plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.05 h	100 mg single, oral		CARMOFUR plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
500 mg/m2 1 times / day multiple, oral Studied dose	unhealthy, 17-70 years	Other AEs: Bladder irritation, Flushing...
300 mg 1 times / day multiple, oral Studied dose	unhealthy, 49-74 years	Other AEs: Anorexia, Nausea and vomiting...
400 mg 1 times / day multiple, oral Studied dose	unhealthy, 53 years	Disc. AE: Leukoencephalopathy...
300 mg/m2 3 times / day multiple, oral MTD	unhealthy, Median age 60 years	DLT: Anemia, Neutropenia...
300 mg/m2 3 times / day multiple, oral MTD	unhealthy, Median age 60 years	DLT: Neutropenia, Fatigue...

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AEs

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AE	Significance	Dose	Population
Angina	0.9%	500 mg/m2 1 times / day multiple, oral Studied dose	unhealthy, 17-70 years
Antabuse effect	0.9%	500 mg/m2 1 times / day multiple, oral Studied dose	unhealthy, 17-70 years
Constipation	0.9%	500 mg/m2 1 times / day multiple, oral Studied dose	unhealthy, 17-70 years
Gastric pain	0.9%	500 mg/m2 1 times / day multiple, oral Studied dose	unhealthy, 17-70 years
Hematuria	0.9%	500 mg/m2 1 times / day multiple, oral Studied dose	unhealthy, 17-70 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 706 OATP1B1 788	AC1/2 1

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1 803	inhibitor 3,277	no
OATP1B3 715	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
AC1/2 1	substrate 3,367	yes

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PubMed

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Title	Date	PubMed
[Clinical evaluation of 1-hexylcarbamoyl-5-fluorouracil (HCFU) in hepatocellular carcinoma].	1984 Nov	6093712
A case of carmofur-induced leukoencephalopathy--MR images and CT findings.	1989 Sep	2487975
Randomized, controlled trial of lateral node dissection vs. nerve-preserving resection in patients with rectal cancer after preoperative radiotherapy.	2001 Sep	11584199
[Postoperative changes in serum lipid levels of breast cancer and adjuvant chemotherapy].	2004 Oct	15508443
1-hexylcarbamoyl-5-fluorouracil + cyclophosphamide + tamoxifen versus CMF + tamoxifen in women with lymph node-positive breast cancer after primary surgery: a randomized controlled trial.	2004 Oct	15375502

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Patents

Sample Use Guides

In Vivo Use Guide

Orally 300-500 mg/m2 daily for 6 weeks for advanced gastrointestinal cancer treatment

Route of Administration: Oral

In Vitro Use Guide

When exposed for 24 h to carmofur (1–100 mM), AC-overexpressing HEK 293 cells showed a markedly reduced ceramide accumulation and cell death relative to control cells subjected to the same treatment.

Substance Class	Chemical
Record UNII	HA82M3RAB2
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

CARMOFUR

Official Name

English

carmofur [INN]

Common Name

English

CARMOFUR [MI]

Common Name

English

NSC-758963

Code

English

MIFUROL

Brand Name

English

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Classification Tree

Code System

Code

Antimetabolite

NCI_THESAURUS

C1557

Pyrimidine analogues

WHO-VATC

QL01BC04

Pyrimidine analogues

WHO-ATC

L01BC04

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Code System

Code

Type

Description

NCI_THESAURUS

C955

PRIMARY

FDA UNII

HA82M3RAB2

PRIMARY

WIKIPEDIA

CARMOFUR

PRIMARY

PUBCHEM

2577

PRIMARY

DRUG CENTRAL

511

PRIMARY

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Related Record

Type

Details


					HA82M3RAB2

CARMOFUR

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

T_1/2

Drug as perpetrator