PAROMOMYCIN

First approved in 1960

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H45N5O14
Molecular Weight	615.6285
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O

InChI

InChIKey=UOZODPSAJZTQNH-LSWIJEOBSA-N

InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H45N5O14
Molecular Weight	615.6285
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	19 / 19
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB01421
Curator's Comment: Description was created based on several sources, including http://www.drugs.com/cdi/paromomycin.html http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20%28General%20Monographs-%20H%29/HUMATIN.html

Paromomycin is a broad spectrum aminoglycoside antibiotic produced by by Streptomyces rimosus var. paromomycinus and used to treat intestinal infections such as cryptosporidiosis and amoebiasis, and other diseases such as leishmaniasis. Paromomycin is also used for the management of hepatic coma as adjunctive therapy. Paromomycin inhibits protein synthesis by binding to bacterial or protozoal 16S ribosomal RNA which causes defective polypeptide chains to be produced. Continuous production of defective proteins eventually leads to bacterial death. Gastrointestinal side effects include nausea, vomiting, diarrhea, and abdominal discomfort.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 180 Target ID: CHEMBL2363135 Sources: http://www.drugbank.ca/drugs/DB01421	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intestinal amebiasis 4 Sources: http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc0f4113-e627-4caf-b2d4-95b4106e57f5	Curative		Approved 8583	PAROMOMYCIN SULFATE Approved Use Paromomycin sulfate is indicated for intestinal amebiasis—acute and chronic (NOTE—It is not effective in extraintestinal amebiasis); management of hepatic coma—as adjunctive therapy. Launch Date 2007
Hepatic coma 6 Sources: http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cc0f4113-e627-4caf-b2d4-95b4106e57f5	Secondary		Approved 8583	PAROMOMYCIN SULFATE Approved Use Paromomycin sulfate is indicated for intestinal amebiasis—acute and chronic (NOTE—It is not effective in extraintestinal amebiasis); management of hepatic coma—as adjunctive therapy. Launch Date 2007

C_max

Value	Dose	Co-administered	Analyte	Population
331 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689	150 mg single, topical dose: 150 mg route of administration: Topical experiment type: SINGLE co-administered:		PAROMOMYCIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1000 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689	150 mg 1 times / day multiple, topical dose: 150 mg route of administration: Topical experiment type: MULTIPLE co-administered:		PAROMOMYCIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2180 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689	150 mg single, topical dose: 150 mg route of administration: Topical experiment type: SINGLE co-administered:		PAROMOMYCIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8575 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689	150 mg 1 times / day multiple, topical dose: 150 mg route of administration: Topical experiment type: MULTIPLE co-administered:		PAROMOMYCIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.04 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689	150 mg single, topical dose: 150 mg route of administration: Topical experiment type: SINGLE co-administered:		PAROMOMYCIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.96 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689	150 mg 1 times / day multiple, topical dose: 150 mg route of administration: Topical experiment type: MULTIPLE co-administered:		PAROMOMYCIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28756612			PAROMOMYCIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052 CYP 303	OCT1 39

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 656	inducer 1966 Sources: https://hekyll.services.adelaide.edu.au/dspace/handle/2440/88837 Page: 71.0	likely

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5754937/ Page: abstract	yes
P-gp 2052	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5754937/ Page: abstract	yes		yes (co-administration study) Comment: verapamil increased paromomycin exposure 1.5x Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5754937/ Page: abstract

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7934	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7934
ChemicalBook	CB6911922	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6911922
eMolecules	4786830	https://www.emolecules.com/cgi-bin/more?vid=4786830
MolPort	MolPort-002-510-747	https://www.molport.com/shop/molecule-link/MolPort-002-510-747
ZINC	ZINC000060183170	http://zinc15.docking.org/substances/ZINC000060183170

PubMed

Title	Date	PubMed
Immunohistochemistry based assay to determine the effects of treatments on Cryptosporidium parvum viability.	2001	11906073
[Treatment of visceral leishmaniasis].	2001 Aug	11535968
Treatment of Giardia lamblia infections.	2001 Feb	11224841
Cgr1p, a novel nucleolar protein encoded by Saccharomyces cerevisiae orf YGL0292w.	2001 Jan	11116400
Combined interleukin-12 and topical chemotherapy for established Leishmaniasis drastically reduces tissue parasitism and relapses in susceptible mice.	2001 Jun 1	11343214
Nitroimidazole-resistant vaginal trichomoniasis treated with paromomycin.	2001 May	11311775
Paromomycin in cryptosporidiosis.	2001 May 15	11317257
Aminoglycoside binding to human and bacterial A-Site rRNA decoding region constructs.	2001 Oct	11557348
Media for the isolation and enumeration of bifidobacteria in dairy products.	2001 Sep 28	11603854
Palmoplantar pruritus subsiding after Blastocystis hominis eradication.	2002	12013204
Chemotherapy of leishmaniasis.	2002	11860369
Topical treatment for cutaneous leishmaniasis.	2002 Apr	12090720
Stereospecificity of aminoglycoside-ribosomal interactions.	2002 Aug 20	12173937
Evaluation of in vitro and in vivo activity of benzindazole-4,9-quinones against Cryptosporidium parvum.	2002 Dec	12461020
Absorption studies on aminoglycoside binding to the packaging region of human immunodeficiency virus type-1.	2002 Feb 25	11844684
Polypeptide synthesis directed by DNA as a messenger in cell-free polypeptide synthesis by extreme thermophiles, Thermus thermophilus HB27 and Sulfolobus tokodaii strain 7.	2002 Jun	12038981
Sequence-specific recognition of the major groove of RNA by deoxystreptamine.	2002 May 21	12009887
Controlling the onset of natural cryptosporidiosis in calves with paromomycin sulphate.	2002 Nov 16	12463536
Selection of tRNA by the ribosome requires a transition from an open to a closed form.	2002 Nov 27	12464183
The protein synthesis inhibitors, oxazolidinones and chloramphenicol, cause extensive translational inaccuracy in vivo.	2002 Sep 13	12217690
Treatment of cutaneous leishmaniasis with aminosidine (paromomycin) ointment: double-blind, randomized trial in the Islamic Republic of Iran.	2003	12856053
Efficacy of antigiardial drugs.	2003 Nov	14585063
Markovian negentropies in bioinformatics. 1. A picture of footprints after the interaction of the HIV-1 Psi-RNA packaging region with drugs.	2003 Nov 1	14594713
[Liver abscess: a practical approach].	2003 Oct 8	14587368

Patents

Sample Use Guides

In Vivo Use Guide

Intestinal amebiasis: 25 to 35 mg/kg body weight daily, administered in three doses with meals, for five to ten days. Management of hepatic coma: 4 g daily in divided doses, given at regular intervals for five to six days.

Route of Administration: Oral

In Vitro Use Guide

1184 mg/L

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:30:14 GMT 2025` Edited by `admin` on `Wed Apr 02 09:30:14 GMT 2025`
Record UNII	61JJC8N5ZK
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ANTIBIOTIC 503-3

Preferred Name

English

PAROMOMYCIN

Official Name

English

R-400

Code

English

CRESTOMYCIN

Common Name

English

CATENULIN

Common Name

English

QUINTOMYCIN C

Common Name

English

ANTIBIOTIC SF-767B

Code

English

PAUCIMYCIN

Common Name

English

PAROMOMYCIN [VANDF]

Common Name

English

DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-O-.BETA.-D-RIBOFURANOSYL-(1->5)-O-(2-AMINO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXYSTREPTAMINE

Common Name

English

GABROMYCIN

Common Name

English

O-2-AMINO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-.BETA.-D-RIBOFURANOSYL-(1->5))-2-DEOXY-D-STREPTAMINE

Common Name

English

NEOMYCIN E

Common Name

English

HYDROXYMYCIN

Common Name

English

NEOMYCIN SULFATE IMPURITY E [EP IMPURITY]

Common Name

English

paromomycin [INN]

Common Name

English

MONOMYCIN A

Common Name

English

AMINOSIDIN

Common Name

English

PAROMOMYCIN [MI]

Common Name

English

D-STREPTAMINE, O-2-AMINO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-.BETA.-D-RIBOFURANOSYL-(1->5))-2-DEOXY-

Common Name

English

PAROMOMYCIN I

Common Name

English

ESTOMYCIN

Common Name

English

Paromomycin [WHO-DD]

Common Name

English

O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-O-.BETA.-D-RIBOFURANOSYL-(1->5)-O-(2-AMINO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXYSTREPTAMINE

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA07AA06