EXATECAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H22FN3O4
Molecular Weight	435.4476
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@]1(O)C(=O)OCC2=C1C=C3N(CC4=C3N=C5C=C(F)C(C)=C6CC[C@H](N)C4=C56)C2=O

InChI

InChIKey=ZVYVPGLRVWUPMP-FYSMJZIKSA-N

InChI=1S/C24H22FN3O4/c1-3-24(31)14-6-18-21-12(8-28(18)22(29)13(14)9-32-23(24)30)19-16(26)5-4-11-10(2)15(25)7-17(27-21)20(11)19/h6-7,16,31H,3-5,8-9,26H2,1-2H3/t16-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C24H22FN3O4
Molecular Weight	435.4476
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11193901 | https://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=778296&p_IsPs=N | https://www.ncbi.nlm.nih.gov/pubmed/15991999

Exatecan (DX-8951f), a new hexacyclic camptothecin analogue, is a second-generation topoisomerase inhibitor that prevents rapidly dividing cells from replicating by interrupting DNA transcription, ultimately leading to cell death. Preclinical studies showed exatecan to have broad-spectrum antitumor efficacy. Exatecan is in phase III clinical trials for the treatment of pancreas cancer. However, there is no recent report of this research. The compound was co-developed by Daiichi Pharmaceutical (now Daiichi Sankyo) and Yakult Honsha.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase I 60 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27599744 \| https://www.ncbi.nlm.nih.gov/pubmed/11193901 \| https://www.ncbi.nlm.nih.gov/pubmed/15991999 \| https://www.ncbi.nlm.nih.gov/pubmed/9330608	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Pancreatic cancer 98 Sources: https://clinicaltrials.gov/ct2/show/NCT00023972	Primary	Phase III 665	Unknown Approved Use Unknown
Gastric cancer 53 Sources: https://clinicaltrials.gov/ct2/show/NCT00017212	Primary	Phase II 1147	Unknown Approved Use Unknown
Sarcoma 14 Sources: https://clinicaltrials.gov/ct2/show/NCT00055939	Primary	Phase II 1147	Unknown Approved Use Unknown
Liver cancer 53 Sources: https://clinicaltrials.gov/ct2/show/NCT00004108	Primary	Phase II 1147	Unknown Approved Use Unknown
Cervical cancer 40 Sources: https://clinicaltrials.gov/ct2/show/NCT00004866	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
4.2 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	0.15 mg/m² single, intravenous dose: 0.15 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
61.2 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	2.4 mg/m² single, intravenous dose: 2.4 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
76.1 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	3 mg/m² single, intravenous dose: 3 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
114.3 ng/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	3.6 mg/m² single, intravenous dose: 3.6 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
118.55 ng/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1 mg/m² single, intravenous dose: 1 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
124.88 ng/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1.33 mg/m² single, intravenous dose: 1.33 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
284.27 ng/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1.77 mg/m² single, intravenous dose: 1.77 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
208.15 ng/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.1 mg/m² single, intravenous dose: 2.1 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
280.1 ng/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.35 mg/m² single, intravenous dose: 2.35 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
279.3 ng/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.75 mg/m² single, intravenous dose: 2.75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
464.7 ng/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	3.13 mg/m² single, intravenous dose: 3.13 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
104 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	0.15 mg/m² single, intravenous dose: 0.15 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1834 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	2.4 mg/m² single, intravenous dose: 2.4 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2302 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	3 mg/m² single, intravenous dose: 3 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5464 ng × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	3.6 mg/m² single, intravenous dose: 3.6 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
775 ng × h/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1 mg/m² single, intravenous dose: 1 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
606 ng × h/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1.33 mg/m² single, intravenous dose: 1.33 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1529 ng × h/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1.77 mg/m² single, intravenous dose: 1.77 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1198 ng × h/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.1 mg/m² single, intravenous dose: 2.1 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1583 ng × h/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.35 mg/m² single, intravenous dose: 2.35 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1095 ng × h/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.75 mg/m² single, intravenous dose: 2.75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3151 ng × h/mL CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	3.13 mg/m² single, intravenous dose: 3.13 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
13.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	0.15 mg/m² single, intravenous dose: 0.15 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
13.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	2.4 mg/m² single, intravenous dose: 2.4 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
13.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	3 mg/m² single, intravenous dose: 3 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
13.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11230496/	3.6 mg/m² single, intravenous dose: 3.6 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8 h CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1 mg/m² single, intravenous dose: 1 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8 h CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1.33 mg/m² single, intravenous dose: 1.33 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8 h CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	1.77 mg/m² single, intravenous dose: 1.77 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8 h CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.1 mg/m² single, intravenous dose: 2.1 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8 h CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.35 mg/m² single, intravenous dose: 2.35 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8 h CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	2.75 mg/m² single, intravenous dose: 2.75 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8 h CLINICAL TRIAL https://www.annalsofoncology.org/article/S0923-7534(19)63544-1/fulltext	3.13 mg/m² single, intravenous dose: 3.13 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	EXATECAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.6 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 0.6 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 0.6 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14586557/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/14586557/	Other AEs: Neutropenia, Leukopenia... Other AEs: Neutropenia (grade 3-4, 50%) Leukopenia (grade 3-4, 50%) Anemia (grade 3, 25%) Thrombocytopenia (grade 3, 13%) Intestinal obstruction (grade 3, 31%) Nausea (grade 3, 25%) Vomiting (grade 3, 19%) Dehydration (grade 3, 19%) Fatigue (grade 3-4, 19%) Neutropenic fever (grade 3, 6%) Sources: https://pubmed.ncbi.nlm.nih.gov/14586557/
0.6 mg/m2 5 times / day multiple, intravenous Highest studied dose Dose: 0.6 mg/m2, 5 times / day Route: intravenous Route: multiple Dose: 0.6 mg/m2, 5 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10963644/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10963644/	Other AEs: Neutropenia, Thrombocytopenia... Other AEs: Neutropenia (grade 4, 33.3%) Thrombocytopenia (grade 4, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/10963644/
0.5 mg/m2 5 times / day multiple, intravenous MTD Dose: 0.5 mg/m2, 5 times / day Route: intravenous Route: multiple Dose: 0.5 mg/m2, 5 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10963644/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10963644/	Other AEs: Neutropenia, Fever... Other AEs: Neutropenia (grade 4, 33.3%) Fever (grade 4, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/10963644/
0.5 mg/m2 1 times / day multiple, intravenous RP2D Dose: 0.5 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 0.5 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12942555/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12942555/	Disc. AE: Neutropenia... AEs leading to discontinuation/dose reduction: Neutropenia (grade 4, 80%) Sources: https://pubmed.ncbi.nlm.nih.gov/12942555/
0.5 mg/m2 1 times / day multiple, intravenous RP2D Dose: 0.5 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 0.5 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12942555/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12942555/	Other AEs: Neutropenia... Other AEs: Neutropenia (grade 4, 33%) Sources: https://pubmed.ncbi.nlm.nih.gov/12942555/

AEs

PubMed

Title	Date	PubMed
A predictive model of human myelotoxicity using five camptothecin derivatives and the in vitro colony-forming unit granulocyte/macrophage assay.	2004-10-01	15475463
A phase IIA study of the topoisomerase I inhibitor, exatecan mesylate (DX-8951f), administered at two different dose schedules in patients with platinum- and taxane-resistant/refractory ovarian cancer.	2004-10	15385119
A phase II study of intravenous exatecan mesylate (DX-8951f) administered daily for 5 days every 3 weeks to patients with advanced ovarian, tubal or peritoneal cancer resistant to platinum, taxane and topotecan.	2004-01	14586557
The activity profile of the hexacyclic camptothecin derivative DX-8951f in experimental human colon cancer and ovarian cancer.	2002-10-15	12234607
The activity profile of the hexacyclic camptothecin derivative DX-8951f in experimental human colon cancer and ovarian cancer.	2002-10-15	12234607
DX-8951f: summary of phase I clinical trials.	2000	11193901

Patents

Sample Use Guides

In Vivo Use Guide

Fifty-seven patients with bidimensionally measurable ovarian cancer, previously exposed to platinum and taxanes, whose disease had relapsed within 6 months of platinum-containing chemotherapy were randomised to one of two intravenous schedules of exatecan mesylate; 0.3 mg/m(2) daily for 5 days every 3 weeks (Arm A) or 2.1 mg/m(2) weekly for 3 weeks out of 4 (Arm B).

Route of Administration: Intravenous

In Vitro Use Guide

Exatecan had superior antitumor efficacy compared to topotecan and irinotecan against all human malignancies tested, with mean IC50 values of 30.8, 48.2, 43.6 and 70.6 ng/ml, respectively, against esophageal, gastric, colorectal and breast cancer lines.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:33:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:33:25 GMT 2025`
Record UNII	OC71PP0F89
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EXATECAN

Official Name

English

DX-8951

Preferred Name

English

Exatecan [WHO-DD]

Common Name

English

exatecan [INN]

Common Name

English

(1S,9S)-1-AMINO-9-ETHYL-5-FLUORO-1,2,3,9,12,15-HEXAHYDRO-9-HYDROXY-4-METHYL-10H,13H-BENZO(DE)PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-10,13-DIONE

Systematic Name

English

EXATECAN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2843