Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Putrescine
- DrugBank Accession Number
- DB01917
- Background
Putrescine is a toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine. Putrescine is a solid. This compound belongs to the polyamines. These are compounds containing more than one amine group. Known drug targets of putrescine include putrescine-binding periplasmic protein, ornithine decarboxylase, and S-adenosylmethionine decarboxylase proenzyme.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Putrescine (DB01917)
- Weight
- Average: 88.1515
Monoisotopic: 88.100048394 - Chemical Formula
- C4H12N2
- Synonyms
- putrescina
- External IDs
- NSC-60545
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AS-adenosylmethionine decarboxylase proenzyme inhibitorHumans AOrnithine decarboxylase inhibitorHumans UBeta-1 adrenergic receptor Not Available Humans UBeta-2 adrenergic receptor Not Available Humans UPutrescine-binding periplasmic protein Not Available Escherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Monoalkylamines
- Alternative Parents
- Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Hydrocarbon derivative / Organopnictogen compound / Primary aliphatic amine
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- alkane-alpha,omega-diamine (CHEBI:17148) / Biogenic amines (C00134) / an aliphatic α,ω-diamine (PUTRESCINE)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- V10TVZ52E4
- CAS number
- 110-60-1
- InChI Key
- KIDHWZJUCRJVML-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2
- IUPAC Name
- butane-1,4-diamine
- SMILES
- NCCCCN
References
- Synthesis Reference
Sang Yup Lee, Zhi Gang Qian, Xiaoxia Xia, Yong Jae Jeon, "MUTANT MICROORGANISMS HAVING A HIGH ABILITY TO PRODUCE PUTRESCINE AND METHOD FOR PRODUCING PUTRESCINE USING THE SAME." U.S. Patent US20100203599, issued August 12, 2010.
US20100203599- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001414
- KEGG Compound
- C02896
- PubChem Compound
- 1045
- PubChem Substance
- 46506728
- ChemSpider
- 13837702
- BindingDB
- 50009385
- ChEBI
- 17148
- ChEMBL
- CHEMBL46257
- ZINC
- ZINC000005828633
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- PUT
- Wikipedia
- Putrescine
- PDB Entries
- 1a99 / 1f3t / 1i72 / 1i79 / 1i7b / 1i7c / 1i7m / 1jl0 / 1msv / 2o06 … show 76 more
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 27.5 °C PhysProp boiling point (°C) 158.5 °C PhysProp logP -0.70 SANGSTER (1994) pKa 10.8 (at 20 °C) PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 236.0 mg/mL ALOGPS logP -0.98 ALOGPS logP -0.85 Chemaxon logS 0.43 ALOGPS pKa (Strongest Basic) 10.51 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 52.04 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 27.38 m3·mol-1 Chemaxon Polarizability 11.07 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8896 Blood Brain Barrier + 0.8645 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.56 P-glycoprotein inhibitor I Non-inhibitor 0.9692 P-glycoprotein inhibitor II Non-inhibitor 0.8872 Renal organic cation transporter Non-inhibitor 0.647 CYP450 2C9 substrate Non-substrate 0.895 CYP450 2D6 substrate Substrate 0.5153 CYP450 3A4 substrate Non-substrate 0.8448 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9497 CYP450 2C19 inhibitor Non-inhibitor 0.9084 CYP450 3A4 inhibitor Non-inhibitor 0.9111 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8704 Ames test Non AMES toxic 0.908 Carcinogenicity Non-carcinogens 0.5694 Biodegradation Not ready biodegradable 0.529 Rat acute toxicity 2.3026 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8553 hERG inhibition (predictor II) Non-inhibitor 0.8449
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 113.2333956 predictedDarkChem Lite v0.1.0 [M-H]- 113.2338956 predictedDarkChem Lite v0.1.0 [M-H]- 113.3238956 predictedDarkChem Lite v0.1.0 [M-H]- 118.99655 predictedDeepCCS 1.0 (2019) [M+H]+ 114.0996956 predictedDarkChem Lite v0.1.0 [M+H]+ 114.0273956 predictedDarkChem Lite v0.1.0 [M+H]+ 114.1102956 predictedDarkChem Lite v0.1.0 [M+H]+ 120.90199 predictedDeepCCS 1.0 (2019) [M+Na]+ 113.5540956 predictedDarkChem Lite v0.1.0 [M+Na]+ 113.7682956 predictedDarkChem Lite v0.1.0 [M+Na]+ 113.7104956 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.92271 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Essential for biosynthesis of the polyamines spermidine and spermine. Promotes maintenance and self-renewal of embryonic stem cells, by maintaining spermine levels
- Specific Function
- Adenosylmethionine decarboxylase activity
- Gene Name
- AMD1
- Uniprot ID
- P17707
- Uniprot Name
- S-adenosylmethionine decarboxylase proenzyme
- Molecular Weight
- 38339.335 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the first and rate-limiting step of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine. Polyamines are essential for cell proliferation and are implicated in cellular processes, ranging from DNA replication to apoptosis
- Specific Function
- Ornithine decarboxylase activity
- Gene Name
- ODC1
- Uniprot ID
- P11926
- Uniprot Name
- Ornithine decarboxylase
- Molecular Weight
- 51147.73 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling. Involved in the regulation of sleep/wake behaviors (PubMed:31473062)
- Specific Function
- Alpha-2a adrenergic receptor binding
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51222.97 Da
References
- Meana C, Bordallo J, Bordallo C, Suarez L, Cantabrana B, Sanchez M: Functional effects of polyamines via activation of human beta1- and beta2-adrenoceptors stably expressed in CHO cells. Pharmacol Rep. 2010 Jul-Aug;62(4):696-706. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
- Specific Function
- Adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Meana C, Bordallo J, Bordallo C, Suarez L, Cantabrana B, Sanchez M: Functional effects of polyamines via activation of human beta1- and beta2-adrenoceptors stably expressed in CHO cells. Pharmacol Rep. 2010 Jul-Aug;62(4):696-706. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Putrescine-importing atpase activity
- Specific Function
- Required for the activity of the bacterial periplasmic transport system of putrescine. Polyamine binding protein.
- Gene Name
- potF
- Uniprot ID
- P31133
- Uniprot Name
- Putrescine-binding periplasmic protein
- Molecular Weight
- 40839.305 Da
References
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transporter that mediates the transport of endogenous and microbial zwitterions and organic cations (PubMed:10215651, PubMed:15107849, PubMed:15795384, PubMed:16729965, PubMed:20601551, PubMed:22206629, PubMed:22569296, PubMed:29530864). Functions as a Na(+)-dependent and pH-dependent high affinity microbial symporter of potent food-derived antioxidant ergothioeine (PubMed:15795384, PubMed:29530864, PubMed:33124720). Transports one sodium ion with one ergothioeine molecule (By similarity). Involved in the absorption of ergothioneine from the luminal/apical side of the small intestine and renal tubular cells, and into non-parenchymal liver cells, thereby contributing to maintain steady-state ergothioneine level in the body (PubMed:20601551). Also mediates the bidirectional transport of acetycholine, although the exact transport mechanism has not been fully identified yet (PubMed:22206629). Most likely exports anti-inflammatory acetylcholine in non-neuronal tissues, thereby contributing to the non-neuronal cholinergic system (PubMed:22206629, PubMed:22569296). Displays a general physiological role linked to better survival by controlling inflammation and oxidative stress, which may be related to ergothioneine and acetycholine transports (PubMed:15795384, PubMed:22206629). May also function as a low-affinity Na(+)-dependent transporter of L-carnitine through the mitochondrial membrane, thereby maintaining intracellular carnitine homeostasis (PubMed:10215651, PubMed:15107849, PubMed:16729965). May contribute to regulate the transport of cationic compounds in testis across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- Acetylcholine transmembrane transporter activity
- Gene Name
- SLC22A4
- Uniprot ID
- Q9H015
- Uniprot Name
- Solute carrier family 22 member 4
- Molecular Weight
- 62154.48 Da
References
- Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22