Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Spermidine
- DrugBank Accession Number
- DB03566
- Background
Spermidine is a polyamine formed from putrescine. It is found in almost all tissues in association with nucleic acids. It is found as a cation at all pH values, and is thought to help stabilize some membranes and nucleic acid structures. It is a precursor of spermine.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Spermidine (DB03566)
- Weight
- Average: 145.2459
Monoisotopic: 145.157897623 - Chemical Formula
- C7H19N3
- Synonyms
- 1,5,10-triazadecane
- 4-azaoctamethylenediamine
- 4-azaoctane-1,8-diamine
- N-(3-Aminopropyl)-1,4-butane-diamine
- N-(3-aminopropyl)butane-1,4-diamine
- Spermidin
- Spermidine
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AThioredoxin reductase 1, cytoplasmic inhibitorHumans UBeta-1 adrenergic receptor Not Available Humans UBeta-2 adrenergic receptor Not Available Humans UGentamicin 3-N-acetyltransferase Not Available Pseudomonas aeruginosa USpermidine/putrescine-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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcyclovir The risk or severity of adverse effects can be increased when Acyclovir is combined with Spermidine. Amantadine The risk or severity of adverse effects can be increased when Amantadine is combined with Spermidine. Chlorpheniramine The risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Spermidine. Choline The risk or severity of adverse effects can be increased when Choline is combined with Spermidine. Choline salicylate The risk or severity of adverse effects can be increased when Choline salicylate is combined with Spermidine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Dialkylamines
- Alternative Parents
- Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Hydrocarbon derivative / Organopnictogen compound / Primary aliphatic amine / Primary amine / Secondary aliphatic amine
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- triamine, polyazaalkane (CHEBI:16610)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- U87FK77H25
- CAS number
- 124-20-9
- InChI Key
- ATHGHQPFGPMSJY-UHFFFAOYSA-N
- InChI
- InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2
- IUPAC Name
- (4-aminobutyl)(3-aminopropyl)amine
- SMILES
- NCCCCNCCCN
References
- Synthesis Reference
Raymond J. Bergeron, Jr., "Methods and intermediates for the preparation of spermidine, homospermidine and norspermidine." U.S. Patent US4505861, issued July, 1981.
US4505861- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001257
- KEGG Compound
- C00315
- PubChem Compound
- 1102
- PubChem Substance
- 46506086
- ChemSpider
- 1071
- BindingDB
- 50009353
- 1483262
- ChEBI
- 16610
- ChEMBL
- CHEMBL19612
- ZINC
- ZINC000001532612
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- SPD
- Wikipedia
- Spermidine
- PDB Entries
- 1bo4 / 1i2x / 1pot / 1poy / 1typ / 293d / 2elg / 2hmp / 2o07 / 2p18 … show 188 more
Clinical Trials
- Clinical Trials
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Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Recruiting Treatment Hypertension 1 somestatus stop reason just information to hide
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) < 25 °C PhysProp boiling point (°C) 129 °C at 1.40E+01 mm Hg PhysProp - Predicted Properties
Property Value Source Water Solubility 32.7 mg/mL ALOGPS logP -0.62 ALOGPS logP -1.1 Chemaxon logS -0.65 ALOGPS pKa (Strongest Basic) 10.68 Chemaxon Physiological Charge 3 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 64.07 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 44.97 m3·mol-1 Chemaxon Polarizability 18.8 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 + 0.9215 Blood Brain Barrier + 0.6345 Caco-2 permeable + 0.7072 P-glycoprotein substrate Non-substrate 0.5094 P-glycoprotein inhibitor I Non-inhibitor 0.9178 P-glycoprotein inhibitor II Non-inhibitor 0.6414 Renal organic cation transporter Non-inhibitor 0.6066 CYP450 2C9 substrate Non-substrate 0.8863 CYP450 2D6 substrate Non-substrate 0.5607 CYP450 3A4 substrate Non-substrate 0.8262 CYP450 1A2 substrate Inhibitor 0.877 CYP450 2C9 inhibitor Non-inhibitor 0.9072 CYP450 2D6 inhibitor Non-inhibitor 0.9502 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9703 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9386 Ames test Non AMES toxic 0.8957 Carcinogenicity Non-carcinogens 0.6436 Biodegradation Ready biodegradable 0.5525 Rat acute toxicity 2.4561 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7691 hERG inhibition (predictor II) Non-inhibitor 0.7739
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 137.830226 predictedDarkChem Lite v0.1.0 [M-H]- 137.598426 predictedDarkChem Lite v0.1.0 [M-H]- 133.21223 predictedDeepCCS 1.0 (2019) [M+H]+ 138.022426 predictedDarkChem Lite v0.1.0 [M+H]+ 138.187326 predictedDarkChem Lite v0.1.0 [M+H]+ 135.6681 predictedDeepCCS 1.0 (2019) [M+Na]+ 138.049826 predictedDarkChem Lite v0.1.0 [M+Na]+ 137.805726 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.5403 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Reduces disulfideprotein thioredoxin (Trx) to its dithiol-containing form (PubMed:8577704). Homodimeric flavoprotein involved in the regulation of cellular redox reactions, growth and differentiation. Contains a selenocysteine residue at the C-terminal active site that is essential for catalysis (Probable). Also has reductase activity on hydrogen peroxide (H2O2) (PubMed:10849437)
- Specific Function
- Fad binding
- Gene Name
- TXNRD1
- Uniprot ID
- Q16881
- Uniprot Name
- Thioredoxin reductase 1, cytoplasmic
- Molecular Weight
- 70905.58 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
- Pseudomonas aeruginosa
- Pharmacological action
- Unknown
- General Function
- Aminoglycoside 3-n-acetyltransferase activity
- Specific Function
- Responsible for gentamicin resistance and has a limited substrate range.
- Gene Name
- aacC1
- Uniprot ID
- P23181
- Uniprot Name
- Gentamicin 3-N-acetyltransferase
- Molecular Weight
- 19441.81 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Polyamine-transporting atpase activity
- Specific Function
- Required for the activity of the bacterial periplasmic transport system of putrescine and spermidine. Polyamine binding protein.
- Gene Name
- potD
- Uniprot ID
- P0AFK9
- Uniprot Name
- Spermidine/putrescine-binding periplasmic protein
- Molecular Weight
- 38866.745 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:11388889, PubMed:11408531, PubMed:12439218, PubMed:12719534, PubMed:15389554, PubMed:16263091, PubMed:16272756, PubMed:16581093, PubMed:19536068, PubMed:21128598, PubMed:23680637, PubMed:24961373, PubMed:34040533, PubMed:9187257, PubMed:9260930, PubMed:9655880). Functions as a pH- and Na(+)-independent, bidirectional transporter (By similarity). Cation cellular uptake or release is driven by the electrochemical potential (i.e. membrane potential and concentration gradient) and substrate selectivity (By similarity). Hydrophobicity is a major requirement for recognition in polyvalent substrates and inhibitors (By similarity). Primarily expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (By similarity). Most likely functions as an uptake carrier in enterocytes contributing to the intestinal elimination of organic cations from the systemic circulation (PubMed:16263091). Transports endogenous monoamines such as N-1-methylnicotinamide (NMN), guanidine, histamine, neurotransmitters dopamine, serotonin and adrenaline (PubMed:12439218, PubMed:24961373, PubMed:35469921, PubMed:9260930). Also transports natural polyamines such as spermidine, agmatine and putrescine at low affinity, but relatively high turnover (PubMed:21128598). Involved in the hepatic uptake of vitamin B1/thiamine, hence regulating hepatic lipid and energy metabolism (PubMed:24961373). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with lower efficency (PubMed:17460754). Also capable of transporting non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). May contribute to the transport of cationic compounds in testes across the blood-testis-barrier (Probable). Also involved in the uptake of xenobiotics tributylmethylammonium (TBuMA), quinidine, N-methyl-quinine (NMQ), N-methyl-quinidine (NMQD) N-(4,4-azo-n-pentyl)-quinuclidine (APQ), azidoprocainamide methoiodide (AMP), N-(4,4-azo-n-pentyl)-21-deoxyajmalinium (APDA) and 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:11408531, PubMed:15389554, PubMed:35469921, PubMed:9260930)
- Specific Function
- (r)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Busch AE, Quester S, Ulzheimer JC, Waldegger S, Gorboulev V, Arndt P, Lang F, Koepsell H: Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1. J Biol Chem. 1996 Dec 20;271(51):32599-604. [Article]
- Li DC, Nichols CG, Sala-Rabanal M: Role of a Hydrophobic Pocket in Polyamine Interactions with the Polyspecific Organic Cation Transporter OCT3. J Biol Chem. 2015 Nov 13;290(46):27633-43. doi: 10.1074/jbc.M115.668913. Epub 2015 Sep 24. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:23