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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H45N5O14
Molecular Weight 615.6294
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PAROMOMYCIN

SMILES

C1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])N)O[C@]2([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O2)O)O)N)O[C@@]3([H])[C@@]([H])([C@@]([H])([C@@]([H])(CO)O3)O[C@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@]([H])(CN)O4)O)O)N)O)O)N

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

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
89
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7701
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
7997
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

1.19759045E12
Secondary
Approved
7997
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

1.19759045E12
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
1223

CYP
231
OCT1
19
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OCT1
488
 likely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
231
 yes
P-gp
1223
 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
Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site.
2001 Aug
Antigiardial drugs.
2001 Dec
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
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
Monitoring drug resistance in leishmaniasis.
2001 Nov
Drug resistance in Indian visceral leishmaniasis.
2001 Nov
Aminoglycoside binding to human and bacterial A-Site rRNA decoding region constructs.
2001 Oct
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
[Recurrent episodes of acidosis with encephalopathy in a hemodialysis program patient with short bowel syndrome].
2002
Topical treatment for cutaneous leishmaniasis.
2002 Apr
The early bactericidal activity of streptomycin.
2002 Aug
Anticryptosporidial prophylactic efficacy of enrofloxacin and paromomycin in chickens.
2002 Feb
"Chemotherapeutic approaches to protozoa: Giardia, Trichomonas and Entamoeba-current level of knowledge and outlook".
2002 Jun
[Intestinal giardiasis. Mini-review].
2002 Jun
Crystal structure of a complex between the aminoglycoside tobramycin and an oligonucleotide containing the ribosomal decoding a site.
2002 Jun
Selection of tRNA by the ribosome requires a transition from an open to a closed form.
2002 Nov 27
Various effects of paromomycin on tmRNA-mediated trans-translation.
2003
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 Apr
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 Aug
Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide.
2003 Feb 28
Comparison of X-ray crystal structure of the 30S subunit-antibiotic complex with NMR structure of decoding site oligonucleotide-paromomycin complex.
2003 Jan
Aminoglycosides suppress tRNA processing in human epidermal keratinocytes in vitro.
2003 Jul-Aug
Treatment of cutaneous leishmaniasis by photodynamic therapy.
2003 Jun
Insights into the decoding mechanism from recent ribosome structures.
2003 May
Aminoglycoside complexation with a DNA.RNA hybrid duplex: the thermodynamics of recognition and inhibition of RNA processing enzymes.
2003 May 28
Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step.
2003 Nov
Efficacy of antigiardial drugs.
2003 Nov
Sfp1 plays a key role in yeast ribosome biogenesis.
2003 Oct
Entamoeba histolytica: an update.
2003 Oct
Current treatment approaches to leishmaniasis.
2003 Oct
The molecular basis for A-site mutations conferring aminoglycoside resistance: relationship between ribosomal susceptibility and X-ray crystal structures.
2003 Oct 6
[Liver abscess: a practical approach].
2003 Oct 8
Neomycin and paromomycin inhibit 30S ribosomal subunit assembly in Staphylococcus aureus.
2003 Sep
Multitarget affinity/specificity screening of natural products: finding and characterizing high-affinity ligands from complex mixtures by using high-performance mass spectrometry.
2003 Sep
Thermodynamics of aminoglycoside-rRNA recognition.
2003 Sep
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
Name Type Language
PAROMOMYCIN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
R-400
Code English
NEOMYCIN SULFATE IMPURITY E [EP]
Common Name English
PAROMOMYCIN [WHO-DD]
Common Name 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
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
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 Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
WHO-ATC A07AA06
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.5.2
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
NCI_THESAURUS C2363
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
FDA ORPHAN DRUG 464314
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
NDF-RT N0000175485
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
Code System Code Type Description
DRUG BANK
DB01421
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
EPA CompTox
7542-37-2
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
INN
939
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
ECHA (EC/EINECS)
231-423-0
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
EVMPD
SUB09630MIG
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
FDA UNII
61JJC8N5ZK
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
LACTMED
Paromomycin
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
PUBCHEM
165580
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
NCI_THESAURUS
C61878
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
ChEMBL
CHEMBL370143
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
CAS
7542-37-2
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
DRUG CENTRAL
2067
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
MESH
D010303
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
MERCK INDEX
M8416
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY Merck Index
RXCUI
7934
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
PAROMOMYCIN
Created by admin on Fri Jun 25 20:35:29 UTC 2021 , Edited by admin on Fri Jun 25 20:35:29 UTC 2021
PRIMARY
ACTIVE MOIETY
Structure of PAROMOMYCIN
SALT/SOLVATE (PARENT)
Structure of PAROMOMYCIN SULFATE
NIH
NCATS
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