PZ0182 Sigma


≥95% (HPLC)

Synonym: 2-Hydroxy-6-methylbenzoic acid [(1S,2R,3R,4S,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[[(dimethylamino)carbonyl]amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentyl]methyl ester, PNU-0015800, U-15800

  • CAS Number 23668-11-3

  • Empirical Formula (Hill Notation) C28H38N4O8

  • Molecular Weight 558.62

  •  MDL number MFCD00158126



Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
assay   ≥95% (HPLC)
form   powder
optical activity   [α]/D +20 to +30° in 95% ethanol
color   white to tan
solubility   DMSO: ≥12 mg/mL
originator   Pfizer
storage temp.   2-8°C


Legal Information

Sold for research purposes under agreement from Pfizer Inc.

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Biochem/physiol Actions

Pactamycin is a potent protein synthesis inhibitor, inhibiting protein synthesis at the translocation step on the 70S ribosome. It has activity against Gram-positive and Gram-negative bacteria, and broad antitumor, antiviral, and antiplasmodial activity. Cytotoxicity limits it clinical use.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®Pfizer), a collection of 90 Pfizer-developed drugs and research tools. Click here to learn more.

This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Price and Availability

DISCOVER Bioactive Small Molecules

Customers Also Viewed

Safety & Documentation

Safety Information

GHS06  GHS06
Signal word 
Hazard statements 
Precautionary statements 
UN 2811 6.1 / PGII
WGK Germany 


Certificate of Analysis

Protocols & Articles


Discover Bioactive Small Molecules for Immunology Research

The immune system is a complex network to detect and defend against non-self pathogenic agents, such as disease-causing viruses, bacteria, and other microorganisms. Various signaling pathways contrib...
Keywords: Antibiotics, Antifungals, Antivirals, Apoptosis, Bioactive small molecules, Cell signaling, Diabetes, Diseases, Immunology, Inflammation

Peer-Reviewed Papers


Set your institution to view full text papers.

Cloning of the pactamycin biosynthetic gene cluster and characterization of a crucial glycosyltransferase prior to a unique cyclopentane ring formation. Kudo F, Kasama Y, Hirayama T, Eguchi T. J. Antibiot. 60, 492-503, (2007)


The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit. Brodersen DE, Clemons WM Jr, Carter AP, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V Cell 103, 1143-1154, (2000)


Biosynthetic Studies and Genetic Engineering of Pactamycin Analogs with Improved Selectivity toward Malarial Parasites. Lu W, Roongsawang N, Mahmud T. Chem. Biol. 18, 425-431, (2011)


Total synthesis of pactamycin. Hanessian S, Vakiti RR, Dorich S, et al. Angew. Chem. Int. Ed. Engl. 50(15), 3497-500, (2011)


Total synthesis of pactamycin and pactamycate: a detailed account. Hanessian S, Vakiti RR, Dorich S, et al. J. Org. Chem. 77(21), 9458-72, (2012)


Probing functional diversity in pactamycin toward antibiotic, antitumor, and antiprotozoal activity. Hanessian S, Vakiti RR, Chattopadhyay AK, et al. Bioorg. Med. Chem. 21(7), 1775-86, (2013)


Crystal structure of a bioactive pactamycin analog bound to the 30S ribosomal subunit. Tourigny DS, Fernández IS, Kelley AC, et al. J. Mol. Biol. 425(20), 3907-10, (2013)


Enantioselective synthesis of pactamycin, a complex antitumor antibiotic. Malinowski JT, Sharpe RJ, and Johnson JS Science 340(6129), 180-2, (2013)


Dissecting the ribosomal inhibition mechanisms of edeine and pactamycin: the universally conserved residues G693 and C795 regulate P-site RNA binding. Dinos G, Wilson DN, Teraoka Y, et al. Mol. Cell. 13(1), 113-24, (2004)


Diastereocontrolled construction of pactamycin's complex ureido triol functional array. Malinowski JT, McCarver SJ, and Johnson JS Org. Lett. 14(11), 2878-81, (2012)


Rapid induction of apoptosis mediated by peptides that bind initiation factor eIF4E. Herbert TP, Fåhraeus R, Prescott A, et al. Curr. Biol. 10(13), 793-6, (2000)


AUG sequences are required to sustain nonsense-codon-mediated suppression of splicing. Kamhi E, Yahalom G, Kass G, et al. Nucleic Acids Res. 34(12), 3421-33, (2006)


Estradiol regulates estrogen receptor mRNA stability. Saceda M, Lindsey RK, Solomon H, et al. J. Steroid Biochem. Mol. Biol. 66(3), 113-20, (1998)


The host gene for intronic U17 small nucleolar RNAs in mammals has no protein-coding potential and is a member of the 5'-terminal oligopyrimidine gene family. Pelczar P and Filipowicz W Mol. Cell. Biol. 18(8), 4509-18, (1998)


Deciphering pactamycin biosynthesis and engineered production of new pactamycin analogues. Ito T, Roongsawang N, Shirasaka N, et al. ChemBioChem. 10(13), 2253-65, (2009)


Synthesis of the oxygenated pactamycin core. Knapp S and Yu Y Org. Lett. 9(7), 1359-62, (2007)


Intracellular Ca(2+) release via the ER translocon activates store-operated calcium entry. Ong HL, Liu X, Sharma A, et al. Pflugers Arch. 453(6), 797-808, (2007)


The phosphorylation of protein S6 modulates the interaction of the 40 S ribosomal subunit with the 5'-untranslated region of a dictyostelium pre-spore-specific mRNA and controls its stability. Chiaberge S, Cassarino E, and Mangiarotti G J. Biol. Chem. 273(42), 27070-5, (1998)


Ribosomal release without peptidyl tRNA hydrolysis at translation termination in a eukaryotic system. Cao J and Geballe AP RNA 4(2), 181-8, (1998)


Pactamycin resistance mutations in functional sites of 16 S rRNA. Mankin AS J. Mol. Biol. 274(1), 8-15, (1997)


Promising lead compounds for novel antiprotozoals. Otoguro K, Iwatsuki M, Ishiyama A, et al. J. Antibiot. 63(7), 381-4, (2010)


Diastereoselective synthesis of vicinal tertiary diols. Loertscher BM, Young PR, Evans PR, et al. Org. Lett. 15(8), 1930-3, (2013)


Analysis of rRNA processing and translation in mammalian cells using a synthetic 18S rRNA expression system. Burman LG and Mauro VP Nucleic Acids Res. 40(16), 8085-98, (2012)


Translational control of terminal oligopyrimidine mRNAs requires a specific regulator. Loreni F and Amaldi F FEBS Lett. 416(3), 239-42, (1997)


Stimulation of Sendai virus C' protein synthesis by cycloheximide. Gupta KC and Ono E Biochem. J. 321 ( Pt 3), 811-8, (1997)


Chemistry. Pactamycin made easy. Codelli JA and Reisman SE Science 340(6129), 152-3, (2013)


Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?