ONDANSETRON HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H19N3O.ClH.2H2O
Molecular Weight	365.854
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O.O.Cl.CN1C2=C(C3=C1C=CC=C3)C(=O)C(CN4C=CN=C4C)CC2

InChI

InChIKey=VRSLTNZJOUZKLX-UHFFFAOYSA-N

InChI=1S/C18H19N3O.ClH.2H2O/c1-12-19-9-10-21(12)11-13-7-8-16-17(18(13)22)14-5-3-4-6-15(14)20(16)2;;;/h3-6,9-10,13H,7-8,11H2,1-2H3;1H;2*1H2

HIDE SMILES / InChI

Molecular Formula	C18H19N3O
Molecular Weight	293.363
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

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

Description

Ondansetron (ZOFRAN®) is a selective 5-HT3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by radiotherapy, anesthesia, surgery or cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties. While its mechanism of action has not been fully characterized, ondansetron is not a dopamine-receptor antagonist. It is not certain whether ondansetron's antiemetic action is mediated centrally, peripherally, or in both sites. However, cytotoxic chemotherapy appears to be associated with release of serotonin from the enterochromaffin cells of the small intestine. The released serotonin may stimulate the vagal afferents through the 5-HT3 receptors and initiate the vomiting reflex.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3a (5-HT3a) receptor 48	Antagonist 2,849		8.31 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Postoperative nausea and vomiting 31	Preventing	Approved 8,583	ZOFRAN
Nausea 63	Preventing	Approved 8,583	ZOFRAN
Vomiting 38	Preventing	Approved 8,583	ZOFRAN

C_max

Value	Dose	Analyte	Population
32.096 ng/mL	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
30.196 ng/mL	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
26.2 ng/mL	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
42.7 ng/mL	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
125.8 ng/mL	24 mg single, oral	ONDANSETRON plasma	Homo sapiens
194.4 ng/mL	24 mg single, oral	ONDANSETRON plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
237.935 ng*h/mL	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
224.155 ng*h/mL	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
293.492 ng*h/mL	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
270.928 ng*h/mL	8 mg single, oral	ONDANSETRON plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.1 h	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
3.5 h	8 mg single, oral	ONDANSETRON plasma	Homo sapiens
4.7 h	24 mg single, oral	ONDANSETRON plasma	Homo sapiens
5.8 h	24 mg single, oral	ONDANSETRON plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
27%	8 mg single, oral		ONDANSETRON plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946		substrate 1,388	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT2 779 OCT1 620 MATE1 415 MATE2 267 OCT3 159	CYP1A1 389 CYP1A2 1,197 P-gp 2,052

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
OCT1 656	inhibitor 4,027	no [IC50 >100 uM]
MATE2 267	inhibitor 4,027	yes [IC50 0.15 uM]	yes (co-administration study)
OCT2 782	inhibitor 4,027	yes [IC50 0.89 uM]
OCT3 161	inhibitor 4,027	yes [IC50 17.4 uM]
MATE1 416	inhibitor 4,027	yes [IC50 6.9 uM]	yes (co-administration study)

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP1A1 389	substrate 4,014	yes
P-gp 2,052	substrate 4,014	yes
CYP1A2 1,197	substrate 4,014	yes	likely (co-administration study)
CYP2D6 1,388	substrate 4,014	yes	likely (co-administration study)
CYP3A4 1,946	substrate 4,014	yes	yes (co-administration study)

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY34510	https://www.001chemical.com/chem/116002-70-1
001 Chemical	DY34512	https://www.001chemical.com/chem/103639-04-9
001 Chemical	DY583739	https://www.001chemical.com/chem/99614-01-4
001 Chemical	NO16446	https://www.001chemical.com/chem/99614-02-5
AA Blocks	AA0065H0	http://www.aablocks.com/goods/Goods/detail?id=AA0065H0

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PubMed

Show entries

Title	Date	PubMed
Ondansetron: a new entity in emesis control.	1990 Nov	2148659
Progress in the control of acute and delayed emesis induced by cisplatin.	1991	1831633
Oral ondansetron in the prevention of postoperative nausea and vomiting.	1992 Nov	1358607
Ondansetron-induced headache. Our experience in gynecological cancer.	1995	7664768
Adjusting the dose of intravenous ondansetron plus dexamethasone to the emetogenic potential of the chemotherapy regimen.	1995 Aug	7636556

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Patents

Sample Use Guides

In Vivo Use Guide

To prevent nausea and vomiting associated with cancer chemotherapy the recommended adult oral dosage of ondansetron (ZOFRAN®) is a single 24-mg tablet administered 30 minutes before the start of single-day highly emetogenic chemotherapy; for moderately emetogenic cancer chemotherapy the recommended adult oral dosage is one 8-mg ondansetron (ZOFRAN®) tablet given twice a day (every 12 hours) for 1 to 2 days after completion of chemotherapy: the first dose should be administered 30 minutes before the start of emetogenic chemotherapy, with a subsequent dose 8 hours after the first dose. To prevent nausea and vomiting associated with radiotherapy the recommended adult oral dosage is one 8-mg ondansetron (ZOFRAN®) tablet given 3 times a day; for total body irradiation, one 8-mg ondansetron (ZOFRAN®) tablet should be administered 1 to 2 hours before each fraction of radiotherapy administered each day; for single high-dose fraction radiotherapy to the abdomen, one 8-mg ondansetron (ZOFRAN®) tablet should be administered 1 to 2 hours before radiotherapy, with subsequent doses every 8 hours after the first dose for 1 to 2 days after completion of radiotherapy; for daily fractionated radiotherapy to the abdomen, one 8-mg ondansetron (ZOFRAN®) tablet should be administered 1 to 2 hours before radiotherapy, with subsequent doses every 8 hours after the first dose for each day radiotherapy is given. To prevent postoperative nausea and vomiting the recommended adult oral dosage is 16 mg given as two 8-mg ondansetron (ZOFRAN®) tablets 1 hour before induction of anesthesia.

Route of Administration: Oral

In Vitro Use Guide

On the isolated vagus nerve and superior cervical ganglion of the rat, R,S-GR38032F (ondansetron) behaved as a reversible competitive antagonist of 5-HT-induced depolarization with pKB values of 8.61+/-0.08 (n=19) and 8.13+/-0.07 (n=16), respectively. The resolved R- and S-isomers of GR38032F were approximately equipotent as 5-HT antagonists on the rat vagus nerve: the pKB values were 8.95+/-0.05 (n=16) and 8.63+/-0.08 (n=17), respectively. R,S-GR38032F was also an effective antagonist of 5-HT on the rabbit isolated vagus nerve: in this case the pKB value was 9.40+/-0.14 (n=4).

Substance Class	Chemical
Record UNII	NMH84OZK2B
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ONDANSETRON HYDROCHLORIDE

Official Name

English

ONDANSETRON HYDROCHLORIDE DIHYDRATE

Preferred Name

English

ONDANSETRON HYDROCHLORIDE DIHYDRATE [MI]

Common Name

English

ONDANSETRON HCL

Common Name

English

GR 38032F

Code

English

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Classification Tree

Code System

Code

Agent Affecting Nervous System

NCI_THESAURUS

C267

Serotonin Antagonist

NCI_THESAURUS

C94726

Subpart B--Compounded Drug Products

CFR

21 CFR 216.24

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Code System

Code

Type

Description

RXCUI

203148

PRIMARY

RxNorm

EVMPD

SUB46120

PRIMARY

SMS_ID

100000131708

PRIMARY

USAN

Y-91

PRIMARY

FDA UNII

NMH84OZK2B

PRIMARY

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Related Record

Type

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					2999F27MAD

ONDANSETRON HYDROCHLORIDE ANHYDROUS

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (HPLC)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [98 to 102] WEIGHT PERCENT (limits)


					2999F27MAD

ONDANSETRON HYDROCHLORIDE ANHYDROUS

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

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Amount:

RELATIONSHIP_AMOUNT [97.5 to 102] WEIGHT PERCENT (limits)


					2999F27MAD

ONDANSETRON HYDROCHLORIDE ANHYDROUS

ANHYDROUS->SOLVATE


					4AF302ESOS

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Amount:

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					098F00IT8F

1,2,3,9-TETRAHYDRO-9-METHYL-3-METHYLENE-4H-CARBAZOL-4-ONE

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Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<0.15] PERCENT PEAK AREA (limits)


					T0049Z45LZ

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					21E15FJP4E

3((DIMETHYLAMINO)METHYL)-1,2,3,9-TETRAHYDRO-9-METHYL-4H-CARBAZOL-4-ONE

IMPURITY -> PARENT

Interaction Type:

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					89VRC1322N

C-DESMETHYLONDANSETRON

IMPURITY -> PARENT

Comments:

sum of impurities A and G: not more than the area of the principal peak in the chromatogram obtained with reference solution (a) (0.2 per cent)

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

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					21E15FJP4E

3((DIMETHYLAMINO)METHYL)-1,2,3,9-TETRAHYDRO-9-METHYL-4H-CARBAZOL-4-ONE

IMPURITY -> PARENT

Comments:

sum of impurities A and G: not more than the area of the principal peak in the chromatogram obtained with reference solution (a) (0.2 per cent)

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator