PAROMOMYCIN SULFATE

First approved in 1960

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H45N5O14.H2O4S
Molecular Weight	713.707
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.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=LJRDOKAZOAKLDU-UDXJMMFXSA-N

InChI=1S/C23H45N5O14.H2O4S/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;1-5(2,3)4/h5-23,29-36H,1-4,24-28H2;(H2,1,2,3,4)/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

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

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

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
Rubisco activase is required for optimal photosynthesis in the green alga Chlamydomonas reinhardtii in a low-CO(2) atmosphere.	2003-12	14605215
Markovian negentropies in bioinformatics. 1. A picture of footprints after the interaction of the HIV-1 Psi-RNA packaging region with drugs.	2003-11-01	14594713
Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step.	2003-11	14638394
Vibrational Markovian modelling of footprints after the interaction of antibiotics with the packaging region of HIV type 1.	2003-11	14607285
Efficacy of antigiardial drugs.	2003-11	14585063
[Liver abscess: a practical approach].	2003-10-08	14587368
The molecular basis for A-site mutations conferring aminoglycoside resistance: relationship between ribosomal susceptibility and X-ray crystal structures.	2003-10-06	14523926
Sfp1 plays a key role in yeast ribosome biogenesis.	2003-10	14555489
Entamoeba histolytica: an update.	2003-10	14502002
Current treatment approaches to leishmaniasis.	2003-10	14501991
Genetic transformation of Indian bread (T. aestivum) and pasta (T. durum) wheat by particle bombardment of mature embryo-derived calli.	2003-09-03	12952555
Neomycin and paromomycin inhibit 30S ribosomal subunit assembly in Staphylococcus aureus.	2003-09	14570276
Multitarget affinity/specificity screening of natural products: finding and characterizing high-affinity ligands from complex mixtures by using high-performance mass spectrometry.	2003-09	14510594
Thermodynamics of aminoglycoside-rRNA recognition.	2003-09	12925993
Effect of antiretroviral protease inhibitors alone, and in combination with paromomycin, on the excystation, invasion and in vitro development of Cryptosporidium parvum.	2003-09	12888587
Evaluation of rye (Secale cereale L.) inbred lines and their crosses for tissue culture response and stable genetic transformation of homozygous rye inbred line L22 by biolistic gene transfer.	2003-08	12830384
Design and synthesis of paromomycin-related heterocycle-substituted aminoglycoside mimetics based on a mass spectrometry RNA-binding assay.	2003-07-28	12888972
Various effects of paromomycin on tmRNA-directed trans-translation.	2003-07-25	12754221
Selective enumeration of Lactobacillus delbrueckii ssp. bulgaricus, Streptococcus thermophilus, Lactobacillus acidophilus, bifidobacteria, Lactobacillus casei, Lactobacillus rhamnosus, and propionibacteria.	2003-07	12906045
Production of Hevea brasiliensis transgenic embryogenic callus lines by Agrobacterium tumefaciens: roles of calcium.	2003-07	12836004
Treatment of cutaneous leishmaniasis by photodynamic therapy.	2003-06	12789181
[Cutaneous leishmaniasis].	2003-06	12759734
Effect of neomycin B on rotavirus plus- and minus-strand RNA synthesis.	2003-06	12756615
Aminoglycoside complexation with a DNA.RNA hybrid duplex: the thermodynamics of recognition and inhibition of RNA processing enzymes.	2003-05-28	12785787
Insights into the decoding mechanism from recent ribosome structures.	2003-05	12765838
Comparative study of the prophylactic and therapeutic effects of paromomycin, recombinant IL-12 alone or in combination against Cryptosporidium parvum infection in immunosuppressed mice.	2003-04	12739805
Eradication of Cryptosporidium in four children with acute lymphoblastic leukemia.	2003-04	12729299
The complex of a designer antibiotic with a model aminoacyl site of the 30S ribosomal subunit revealed by X-ray crystallography.	2003-03-26	12643685
Coupling of drug protonation to the specific binding of aminoglycosides to the A site of 16 S rRNA: elucidation of the number of drug amino groups involved and their identities.	2003-03-07	12595251
Long-lasting anticryptosporidial activity of nitazoxanide in an immunosuppressed rat model.	2003-03	12735719
Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide.	2003-02-28	12589761
A dispensable yeast ribosomal protein optimizes peptidyltransferase activity and affects translocation.	2003-01-31	12433929
HIV-1 RNA dimerization initiation site is structurally similar to the ribosomal A site and binds aminoglycoside antibiotics.	2003-01-24	12435744
Treatment of cutaneous leishmaniasis with either topical paromomycin or intralesional meglumine antimoniate.	2003-01	12558620
Comparison of X-ray crystal structure of the 30S subunit-antibiotic complex with NMR structure of decoding site oligonucleotide-paromomycin complex.	2003-01	12517339
Various effects of paromomycin on tmRNA-mediated trans-translation.	2003	14510467
Treatment of cutaneous leishmaniasis with aminosidine (paromomycin) ointment: double-blind, randomized trial in the Islamic Republic of Iran.	2003	12856053
Evaluation of in vitro and in vivo activity of benzindazole-4,9-quinones against Cryptosporidium parvum.	2002-12	12461020
Selection of tRNA by the ribosome requires a transition from an open to a closed form.	2002-11-27	12464183
Controlling the onset of natural cryptosporidiosis in calves with paromomycin sulphate.	2002-11-16	12463536
Detecting ligand binding to a small RNA target via saturation transfer difference NMR experiments in D(2)O and H(2)O.	2002-11-13	12418877
Footprinting and circular dichroism studies on paromomycin binding to the packaging region of human immunodeficiency virus type-1.	2002-11	12213482
Treatment of asymptomatic intestinal Entamoeba histolytica infection.	2002-10-24	12397207
Aminoglycosides suppress tRNA processing in human epidermal keratinocytes in vitro.	2002-10-22	12784065
The protein synthesis inhibitors, oxazolidinones and chloramphenicol, cause extensive translational inaccuracy in vivo.	2002-09-13	12217690
Identification of a role for actin in translational fidelity in yeast.	2002-09	12242494
Stereospecificity of aminoglycoside-ribosomal interactions.	2002-08-20	12173937
Fluconazole for the treatment of cutaneous leishmaniasis.	2002-08-01	12151480
"Chemotherapeutic approaches to protozoa: Giardia, Trichomonas and Entamoeba-current level of knowledge and outlook".	2002-06	12152617
[Considerations and results of the use of paramomycin in the prevention of infectious complications in colorectal surgery].	2002-04	12164005

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 `Mon Mar 31 17:47:03 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:03 GMT 2025`
Record UNII	845NU6GJPS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMINOSIDINE

Preferred Name

English

PAROMOMYCIN SULFATE

Common Name

English

METALCAPTASE

Common Name

English

GABBROMYCIN

Brand Name

English

HUMATIN

Brand Name

English

GABBROMICINA

Brand Name

English

PAROMOMYCIN SULFATE [JAN]

Common Name

English

FARMINOSIDIN

Brand Name

English

PAROMOMYCIN SULPHATE IS THE SULPHATE SALT OF AN ANTIBIOTIC SUBSTANCE OR SUBSTANCES PRODUCED BY THE GROWTH OF STREPTOMYCES RIMOSUS VAR. PAROMOMYCINUS, OR A MIXTURE OF TWO OR MORE SUCH SALTS

Common Name

English

FARMIGLUCIN

Brand Name

English

1600 ANTIBIOTIC

Code

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-, SULPHATE (SALT)

Common Name

English

NSC-758421

Code

English

PARAMOMYCIN SULPHATE

Common Name

English

PARGONYL

Brand Name

English

SINOSID

Brand Name

English

FI-5853

Code

English

PAROMOMYCIN SULFATE [USP MONOGRAPH]

Common Name

English

PAROMOMYCIN SULFATE [ORANGE BOOK]

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 SULPHATE (SALT)

Common Name

English

PAROMOMYCIN SULFATE [VANDF]

Common Name

English

PARAMICINA

Brand Name

English

HUMAGEL

Brand 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 SULFATE (SALT)

Common Name

English

PAROMOMYCIN SULFATE [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-, SULFATE (SALT)

Common Name

English

PAROMOMYCIN SULFATE [USP-RS]

Common Name

English

PAROMOMYCIN SULFATE IS THE SULFATE SALT OF AN ANTIBIOTIC SUBSTANCE OR SUBSTANCES PRODUCED BY THE GROWTH OF STREPTOMYCES RIMOSUS VAR. PAROMOMYCINUS, OR A MIXTURE OF TWO OR MORE SUCH SALTS

Common Name

English

D-STREPTAMINE, 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-DEOXY-, SULFATE (1:1)

Systematic Name

English

AMINOXIDIN

Brand Name

English

PAROMOMYCIN SULFATE [WHO-IP]

Common Name

English

Paromomycin sulfate [WHO-DD]

Common Name

English

PAROMOMYCIN SULFATE [MART.]

Common Name

English

PAROMOMYCINI SULFAS [WHO-IP LATIN]

Common Name

English

PAROMOMYCIN SULPHATE

Common Name

English

GABBRORAL

Brand Name

English

PARICINA

Brand Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

77193