U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of PAROMOMYCIN

SMILES

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

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
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

Parke Davis
57
Curator's Comment: Paromomycin was discovered by Parke Davis now Pfizer and introduced as Humatin in 1960.

Approval Year

1960
107
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
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
Secondary
Approved
8429
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28756612
PAROMOMYCIN unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1537

CYP
270
OCT1
35
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OCT1
543
 likely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 yes
P-gp
1537
 yes
yes (co-administration study)
Comment: verapamil increased paromomycin exposure 1.5x
Page: abstract
Sourcing

Sourcing

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

PubMed

TitleDatePubMed
Field trial on the therapeutic efficacy of paromomycin on natural Cryptosporidium parvum infections in lambs.
2000 Jun 27
Drug-RNA footprinting.
2001
Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site.
2001 Aug
[Treatment of visceral leishmaniasis].
2001 Aug
eEF1A Controls ascospore differentiation through elevated accuracy, but controls longevity and fruiting body formation through another mechanism in Podospora anserina.
2001 Aug
Cgr1p, a novel nucleolar protein encoded by Saccharomyces cerevisiae orf YGL0292w.
2001 Jan
Which aminoglycoside ring is most important for binding? A hydropathic analysis of gentamicin, paromomycin, and analogues.
2001 Jan 22
Genetic interaction between yeast Saccharomyces cerevisiae release factors and the decoding region of 18 S rRNA.
2001 Jan 26
Combined interleukin-12 and topical chemotherapy for established Leishmaniasis drastically reduces tissue parasitism and relapses in susceptible mice.
2001 Jun 1
Structural origins of aminoglycoside specificity for prokaryotic ribosomes.
2001 Mar 9
Nitroimidazole-resistant vaginal trichomoniasis treated with paromomycin.
2001 May
Paromomycin in cryptosporidiosis.
2001 May 15
Recognition of cognate transfer RNA by the 30S ribosomal subunit.
2001 May 4
A role for the Ppz Ser/Thr protein phosphatases in the regulation of translation elongation factor 1Balpha.
2001 May 4
Randomized, controlled, double-blind trial of topical treatment of cutaneous leishmaniasis with paromomycin plus methylbenzethonium chloride ointment in Guatemala.
2001 Nov
Dual function of eIF3j/Hcr1p in processing 20 S pre-rRNA and translation initiation.
2001 Nov 16
Aminoglycoside binding to human and bacterial A-Site rRNA decoding region constructs.
2001 Oct
Tinidazole therapy for metronidazole-resistant vaginal trichomoniasis.
2001 Oct 15
A Streptomyces rimosus aphVIII gene coding for a new type phosphotransferase provides stable antibiotic resistance to Chlamydomonas reinhardtii.
2001 Oct 17
Media for the isolation and enumeration of bifidobacteria in dairy products.
2001 Sep 28
Leishmaniasis: recognition and management with a focus on the immunocompromised patient.
2002
Fluconazole for the treatment of cutaneous leishmaniasis.
2002 Aug 1
Anticryptosporidial prophylactic efficacy of enrofloxacin and paromomycin in chickens.
2002 Feb
Binding of aminoglycoside antibiotics to the small ribosomal subunit: a continuum electrostatics investigation.
2002 Feb 20
"Chemotherapeutic approaches to protozoa: Giardia, Trichomonas and Entamoeba-current level of knowledge and outlook".
2002 Jun
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
Thermodynamics of aminoglycoside and acyl-coenzyme A binding to the Salmonella enterica AAC(6')-Iy aminoglycoside N-acetyltransferase.
2002 Jun 11
In vitro susceptibility to pentavalent antimony in Leishmania infantum strains is not modified during in vitro or in vivo passages but is modified after host treatment with meglumine antimoniate.
2002 May 2
Sequence-specific recognition of the major groove of RNA by deoxystreptamine.
2002 May 21
Detecting ligand binding to a small RNA target via saturation transfer difference NMR experiments in D(2)O and H(2)O.
2002 Nov 13
Eradication of Cryptosporidium in four children with acute lymphoblastic leukemia.
2003 Apr
Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide.
2003 Feb 28
HIV-1 RNA dimerization initiation site is structurally similar to the ribosomal A site and binds aminoglycoside antibiotics.
2003 Jan 24
Aminoglycosides suppress tRNA processing in human epidermal keratinocytes in vitro.
2003 Jul-Aug
Aminoglycoside complexation with a DNA.RNA hybrid duplex: the thermodynamics of recognition and inhibition of RNA processing enzymes.
2003 May 28
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
Current treatment approaches to leishmaniasis.
2003 Oct
Genetic transformation of Indian bread (T. aestivum) and pasta (T. durum) wheat by particle bombardment of mature embryo-derived calli.
2003 Sep 3
Patents

Patents

JP2010531845A
7

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Additional resource: http://www.rxlist.com/paromomycin-sulfate-drug.htm
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
Curator's Comment: Paromomycin inhibited the growth of Cryptosporidium parvum in Madin-Darby canine kidney (MDCK) cells in a dose-dependent manner. The EC50s of paromomycin against C. parvum growth in MDCK cells was 1184 mg/L. Paromomycin at 25, 50 and 100 μg/ml, inhibited the growth of Leishmania major amastigotes by 34.5%, 61.2%, 74.9% and 85.4%, 89.9%, 95.7% on the 2nd and the 4th day of treatment in culture, respectively (http://www.sciencedirect.com/science/article/pii/S0014489406003262).
1184 mg/L
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:45:21 GMT 2023
Edited
by admin
on Sat Dec 16 17:45:21 GMT 2023
Record UNII
61JJC8N5ZK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PAROMOMYCIN
INN   MI   VANDF   WHO-DD  
INN  
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
ANTIBIOTIC 503-3
Code 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
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
WHO-ATC A07AA06
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 6.5.2
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
NCI_THESAURUS C2363
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
FDA ORPHAN DRUG 464314
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
NDF-RT N0000175485
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
Code System Code Type Description
DRUG BANK
DB01421
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023424
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
INN
939
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
ECHA (EC/EINECS)
231-423-0
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
EVMPD
SUB09630MIG
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
FDA UNII
61JJC8N5ZK
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
LACTMED
Paromomycin
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
PUBCHEM
165580
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
CHEBI
7934
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
NCI_THESAURUS
C61878
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
DAILYMED
61JJC8N5ZK
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL370143
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
SMS_ID
100000082818
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
CAS
7542-37-2
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
DRUG CENTRAL
2067
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
MESH
D010303
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
MERCK INDEX
m8416
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY Merck Index
RXCUI
7934
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
PAROMOMYCIN
Created by admin on Sat Dec 16 17:45:22 GMT 2023 , Edited by admin on Sat Dec 16 17:45:22 GMT 2023
PRIMARY
Related Record Type Details
Structure of PAROMOMYCIN SULFATE
SALT/SOLVATE -> PARENT
Related Record Type Details
NEOMYCIN SULFATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of PAROMOMYCIN
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