SAPACITABINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H42N4O5
Molecular Weight	490.6355
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2C#N

InChI

InChIKey=LBGFKUUHOPIEMA-PEARBKPGSA-N

InChI=1S/C26H42N4O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-23(32)28-22-16-17-30(26(34)29-22)25-20(18-27)24(33)21(19-31)35-25/h16-17,20-21,24-25,31,33H,2-15,19H2,1H3,(H,28,29,32,34)/t20-,21+,24-,25+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://investor.cyclacel.com/news-releases/news-release-details/cyclacel-pharmaceuticals-announces-fda-orphan-drug-designation | https://www.ncbi.nlm.nih.gov/pubmed/26523431 | https://www.ashclinicalnews.org/online-exclusives/sapacitabine-fails-to-meet-primary-endpoint-in-clinical-trial-of-older-aml-patients/https://www.ncbi.nlm.nih.gov/pubmed/22739266 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C82697 | https://www.cyclacel.com/research_programs_oncology_cyc682.shtml

CNDAC (TAK-109) is an analog of the nucleoside deoxycytidine with potential antineoplastic activity. CNDAC is incorporated into DNA and induces single-strand breaks, which are converted into double-strand breaks (DSBs) when cells go through a second S phase. This results in the cell cycle arrest in the S and G2/M phases, DNA fragmentation, and tumor cell apoptosis. Sapacitabine, a prodrug of CNDAC, is being developed by the US biotechnology company Cyclacel for the treatment of hemalogical cancers and solid tumors.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human herpesvirus 8 3 Target ID: CHEMBL612780 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17402726	Inhibitor 8504		0.13 µM [IC50]
DNA 282 Target ID: DNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/22739266	Binding Agent 1076

C_max

Value	Dose	Analyte	Population
2.58 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.43 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	125 mg 2 times / day steady-state, oral dose: 125 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
17.635 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	325 mg single, oral dose: 325 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.88 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	325 mg 2 times / day steady-state, oral dose: 325 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
14.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	375 mg single, oral dose: 375 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
25.45 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	425 mg single, oral dose: 425 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.77 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	475 mg single, oral dose: 475 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.52 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	67 mg/m² single, oral dose: 67 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.09 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	90 mg/m² single, oral dose: 90 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.48 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	120 mg/m² single, oral dose: 120 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.76 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	160 mg/m² single, oral dose: 160 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.35 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	220 mg/m² single, oral dose: 220 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.1 ng/mL EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-8219-0	40 mg/m² 1 times / day steady-state, oral dose: 40 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
581.1 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
774.7 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	125 mg 2 times / day steady-state, oral dose: 125 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5009.125 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	325 mg single, oral dose: 325 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3437 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	325 mg 2 times / day steady-state, oral dose: 325 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1671 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	375 mg single, oral dose: 375 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5894.5 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	425 mg single, oral dose: 425 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
536 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933907/	475 mg single, oral dose: 475 mg route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.22 mg × h/L EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	67 mg/m² single, oral dose: 67 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
24 mg × h/L EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	90 mg/m² single, oral dose: 90 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
42.8 mg × h/L EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	120 mg/m² single, oral dose: 120 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
32 mg × h/L EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	160 mg/m² single, oral dose: 160 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
19.32 mg × h/L EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	220 mg/m² single, oral dose: 220 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11 mg × h/L EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-8219-0	40 mg/m² 1 times / day steady-state, oral dose: 40 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
4.36 h EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	67 mg/m² single, oral dose: 67 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.21 h EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	90 mg/m² single, oral dose: 90 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.38 h EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	120 mg/m² single, oral dose: 120 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.15 h EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	160 mg/m² single, oral dose: 160 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.28 h EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-5392-0	220 mg/m² single, oral dose: 220 mg/m² route of administration: Oral experiment type: SINGLE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.6 h EXPERIMENT https://link.springer.com/article/10.1007/s10637-006-8219-0	40 mg/m² 1 times / day steady-state, oral dose: 40 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered:	SAPACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

PubMed

Title	Date	PubMed
The efficacy of sapacitabine in treating patients with acute myeloid leukemia.	2018-11	30222471
Sapacitabine in the treatment of acute myeloid leukemia.	2015	26523431
Sapacitabine for cancer.	2012-04	22329458

Patents

Sample Use Guides

In Vivo Use Guide

oral sapacitabine capsules

Route of Administration: Oral

Name

Type

Language

CS-682

Preferred Name

English

SAPACITABINE

Official Name

English

N-(1-(2-CYANO-2-DEOXY-.BETA.-D-ARABINOFURANOSYL)-2-OXO-1,2-DIHYDROPYRIMIDIN-4- YL)HEXADECANAMIDE

Common Name

English

CYC-682

Code

English

HEXADECANAMIDE, N-(1-(2-CYANO-2-DEOXY-.BETA.-D-ARABINOFURANOSYL)-1,2-DIHYDRO-2-OXO-4- PYRIMIDINYL)-

Common Name

English

Sapacitabine [WHO-DD]

Common Name

English

CYC682

Code

English

SAPACITABINE [USAN]

Common Name

English

sapacitabine [INN]

Common Name

English

SAPACITABINE [MART.]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/08/557