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Paromomycin

Paromomycin structure

CAS No:
7542-37-2
Formula:
C23H45N5O14
Chemical Name:
Paromomycin
Synonyms:
D-Streptamine,O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2-amino-2-deoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-;Hydroxymycin;Streptamine,O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2-amino-2-deoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-;Zygomycin A1;D-Streptamine,O-2-amino-2-deoxy-α-D-glucopyranosyl-(1→4)-O-[O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-β-D-ribofuranosyl-(1→5)]-2-deoxy-;O-2,6-Diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2-amino-2-deoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-D-streptamine;Paromomycin;Paromomycine;Paromomycin I;Aminosidine I;Antibiotic 2230D;Gabbromycin;Neomycin E;Aminosidine;Gabromycin;Antibiotic SF 767B;Monomycin A;Aminosidin;Humycin;Quintomycin C;Antibiotic 503-3;Gabbromicina;Amminosidin;Paucimycin;Crestomycin;R 400;Catenulin;59-04-1;1389-70-4;1390-73-4;1391-98-6;10010-79-4;11002-84-9;11002-85-0;11021-48-0;11035-13-5;25329-75-3
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Solid

Paromomycin is an amino cyclitol glycoside that is the 1-O-(2-amino-2-deoxy-alpha-D-glucopyranoside) and the 3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranoside of 4,6-diamino-2,3-dihydroxycyclohexane (the 1R,2R,3S,4R,6S diastereoisomer). It is obtained from various Streptomyces species. A broad-spectrum antibiotic, it is used (generally as the sulfate salt) for the treatment of acute and chronic intestinal protozoal infections, but is not effective for extraintestinal protozoal infections. It is also used as a therapeutic against visceral leishmaniasis. It has a role as an antibacterial drug, an antiprotozoal drug, an anthelminthic drug and an antiparasitic agent. It is an aminoglycoside antibiotic and an amino cyclitol glycoside. It derives from a streptamine.|Paromomycin is an Antiprotozoal.|Paromomycin is an aminoglycoside antibiotic derived from Streptomyces rimosus var. paromomycinus, with amebicidal and antibacterial activity. Paromomycin binds specifically to the RNA oligonucleotide at the A site of bacterial 30S ribosomes, thereby causing misreading and premature termination of translation, thereby leading to inhibition of protein synthesis followed by cell death.|An aminoglycoside antibacterial and antiprotozoal agent produced by species of STREPTOMYCES.

Paromomycin Basic Attributes

Molecular Weight：

615.62800

Exact Mass：

615.63

EC Number：

231-423-0

UNII：

61JJC8N5ZK

DSSTox ID：

DTXSID8023424

NCI Thesaurus Code：

C61878

ATC Code：

A07AA06|A - Alimentary tract and metabolism

Characteristics

PSA：

347.32000

XLogP3：

-5.36020

Density：

1.64g/cm3

Boiling Point：

939.8ºC

Flash Point：

522.2ºC

Refractive Index：

1.676

Water Solubility：

7.97e+01 g/L

Collision Cross Section：

239.1 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|237.7 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]

Drug Information

Drug Indication：

For the treatment of acute and chronic intestinal amebiasis (it is not effective in extraintestinal amebiasis). Also for the management of hepatic coma as adjunctive therapy.

Pharmacology：

Paromomycin is a broad spectrum aminoglycoside antibiotic produced by Streptomyces rimosus var. paromomycinus. The in vitro and in vivo antibacterial action of paromomycin closely parallels that of neomycin.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

Absorption：

Poorly absorbed after oral administration, with almost 100% of the drug recoverable in the stool.

Mechanism of Action：

Paromomycin inhibits protein synthesis by binding to 16S ribosomal RNA. Bacterial proteins are synthesized by ribosomal RNA complexes which are composed of 2 subunits, a large subunit (50s) and small (30s) subunit, which forms a 70s ribosomal subunit. tRNA binds to the top of this ribosomal structure. Paramomycin binds to the A site, which causes defective polypeptide chains to be produced. Continuous production of defective proteins eventually leads to bacterial death.

MeSH Entry Terms：

Aminosidine

Paromomycin Use and Manufacturing

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:615.6
XLogP3:-8.7
Hydrogen Bond Donor Count:13
Hydrogen Bond Acceptor Count:19
Rotatable Bond Count:9
Exact Mass:615.29630113
Monoisotopic Mass:615.29630113
Topological Polar Surface Area:347
Heavy Atom Count:42
Complexity:870
Defined Atom Stereocenter Count:19
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes