Betamethasone phosphate
Identification
- Name
- Betamethasone phosphate
- Accession Number
- DB14669
- Description
Betamethasone phosphate is a prodrug that is rapidly hydrolyzed, providing rapidly accessible betamethasone to agonize glucocorticoid receptors.5 Betamethasone provides greater anti-inflammatory activity than prednisolone with less sodium and water retention.5
Betamethasone sodium phosphate was granted FDA approval on 3 March 1965.5
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
- Weight
- Average: 472.446
Monoisotopic: 472.166233087 - Chemical Formula
- C22H30FO8P
- Synonyms
- Betamethasone 21-(dihydrogen phosphate)
- Betamethasone 21-phosphate
- Betamethasone dihydrogen phosphate
Pharmacology
- Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset
- Indication
Betamethasone phosphate is indicated intramuscularly to treat allergic states, dermatologic diseases, endocrine disorders, gastrointestinal diseases, hematologic disorders, neoplastic diseases, nervous system conditions, ophthalmic diseases, renal diseases, respiratory diseases, rheumatic disorders, trichinosis with neurologic or myocardial involvement, and tuberculous meningitis with subarachnoid block or impending block.5 It is also used intra-articularly in the treatment of acute gouty arthritis, acute and subacute bursitis, acute nonspecific tenosynovitis, epicondylitis, rheumatoid arthritis, and synovitis of osteoarthritis.5 Intralesional betamethasone phospahte is indicated in the treatment of alopecia areata, discoid lupus erythematosus, keloids, lichen planus, lichen simplex chronicus, psoriatic plaques, necrobiosis lipoidica diabeticorum, and localized hypertrophic, infiltrated, inflammatory lesions of granuloma annulare.5
- Associated Conditions
- Acute Gouty Arthritis
- Allergic Conditions
- Alopecia Areata (AA)
- Dermatological Disease
- Discoid Lupus Erythematosus (DLE)
- Endocrine Disorders
- Epicondylitis
- Gastrointestinal Diseases
- Haematological disorders
- Keloid Scars
- Kidney Diseases
- Lichen Planus (LP)
- Lichen simplex chronicus
- Necrobiosis lipoidica diabeticorum
- Neoplastic Disease
- Nervous System Disorders
- Ophthalmic Diseases
- Psoriatic plaque
- Respiratory Diseases
- Rheumatism
- Rheumatoid Arthritis
- Acute Bursitis
- Acute nonspecific tenosynovitis
- Cystic tumors of aponeurosis
- Cystic tumors of tendon
- Localized Hypertrophic, Inflammatory, Infiltrated granuloma annulare lesions
- Subacute Bursitis
- Synovitis of osteoarthritis
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
- Pharmacodynamics
Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals.2 Betamethasone phosphate has a short duration of action as it is rapidly hydrolyzed to betamethasone.5 Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces.2 Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.2
- Mechanism of action
Betamethasone phosphate is a soluble ester prodrug of betamethasone.5 Betamethasone is rapidly de-esterified, allowing betamethasone to act as an agonist of the glucocorticoid receptor.5 The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation.2 Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days.2
Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10.2
Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive.2 High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.2
Target Actions Organism UGlucocorticoid receptor agonistHumans UAnnexin A1 agonistHumans - Absorption
An intramuscular injection of 3mg betamethasone acetate and 3mg betametasone phosphate reaches a betamethasone Cmax 33.21 ± 8.71 ng/mL, with a Tmax of 1.56 ± 1.32 h, and an AUC of 506.95 ± 125.03 ng*h/mL.1
- Volume of distribution
The volume of distribution of betamethasone in an intramuscular injection of 3mg betamethasone acetate and 3mg betamethasone phosphate is 226.00 ± 61.64 L.1
- Protein binding
Corticosteroids are generally bound to corticosteroid binding globulin3 and serum albumin4 in plasma.
- Metabolism
Betamethasone phosphate is rapidly de-esterified to betamethasone.5
Hover over products below to view reaction partners
- Route of elimination
Corticosteroids are eliminated predominantly in the urine.4
- Half-life
The half life of betamethasone in an intramuscular injection of 3mg betamethasone acetate and 3mg betamethasone phosphate is 12.47 ± 1.91 h.1
- Clearance
The clearance of betamethasone in an intramuscular injection of 3mg betamethasone acetate and 3mg betamethasone phosphate is 12.62 ± 3.45 L/h.1
- Adverse Effects
- Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data
- Toxicity
Patients experiencing an acute overdose should be treated with symptomatic and supportive treatment.5 Chronic overdoses where patients require continued therapy can be treated through temporary dose reduction or alternate day treatment.5
The oral, intraperitoneal, and intravenous LD50 values in rats are 1877 mg/kg, 1179 mg/kg, and 1276 mg/kg, respectively.6
- Affected organisms
- Not Available
- Pathways
- Not Available
- 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 softwareAbemaciclib The metabolism of Abemaciclib can be increased when combined with Betamethasone phosphate. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Betamethasone phosphate. Acarbose The risk or severity of hyperglycemia can be increased when Betamethasone phosphate is combined with Acarbose. Aceclofenac The risk or severity of gastrointestinal irritation can be increased when Betamethasone phosphate is combined with Aceclofenac. Acemetacin The risk or severity of gastrointestinal irritation can be increased when Betamethasone phosphate is combined with Acemetacin. Acenocoumarol Betamethasone phosphate may increase the anticoagulant activities of Acenocoumarol. Acetohexamide The risk or severity of hyperglycemia can be increased when Betamethasone phosphate is combined with Acetohexamide. Acetyldigitoxin The risk or severity of adverse effects can be increased when Betamethasone phosphate is combined with Acetyldigitoxin. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Betamethasone phosphate is combined with Acetylsalicylic acid. Adenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Betamethasone phosphate. Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- No interactions found.
Categories
- Drug Categories
- Adrenal Cortex Hormones
- Corticosteroids
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Glucocorticoids
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- OAT3/SLC22A8 Substrates
- P-glycoprotein inducers
- P-glycoprotein substrates
- Pregnadienes
- Pregnadienetriols
- Pregnanes
- Steroids
- Steroids, Fluorinated
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Pregnane steroids
- Direct Parent
- Gluco/mineralocorticoids, progestogins and derivatives
- Alternative Parents
- 20-oxosteroids / 11-beta-hydroxysteroids / 17-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Glycerone phosphates / Monoalkyl phosphates / Tertiary alcohols / Alpha-hydroxy ketones show 8 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl fluoride show 26 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 11beta-hydroxy steroid, 17alpha-hydroxy steroid, 20-oxo steroid, steroid phosphate, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid (CHEBI:68603)
Chemical Identifiers
- UNII
- YJO1F9W10R
- CAS number
- 360-63-4
- InChI Key
- VQODGRNSFPNSQE-DVTGEIKXSA-N
- InChI
- InChI=1S/C22H30FO8P/c1-12-8-16-15-5-4-13-9-14(24)6-7-19(13,2)21(15,23)17(25)10-20(16,3)22(12,27)18(26)11-31-32(28,29)30/h6-7,9,12,15-17,25,27H,4-5,8,10-11H2,1-3H3,(H2,28,29,30)/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
- IUPAC Name
- {2-[(1R,2S,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]-2-oxoethoxy}phosphonic acid
- SMILES
- [H][C@@]12C[C@H](C)[C@](O)(C(=O)COP(O)(O)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
References
- General References
- Salem II, Najib NM: Pharmacokinetics of betamethasone after single-dose intramuscular administration of betamethasone phosphate and betamethasone acetate to healthy subjects. Clin Ther. 2012 Jan;34(1):214-20. doi: 10.1016/j.clinthera.2011.11.022. Epub 2011 Dec 9. [PubMed:22154197]
- Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [PubMed:30285357]
- Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [PubMed:23300763]
- Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [PubMed:15634032]
- FDA Approved Drug Products: Celestone Soluspan (betamethasone sodium phosphate and betamethasone acetate) injectable suspension [Link]
- British Pharmacopoeia: Betamethasone Sodium Phosphate MSDS [Link]
- External Links
- ChemSpider
- 96937
- ChEBI
- 68603
- ChEMBL
- CHEMBL1201207
- ZINC
- ZINC000004097469
- Wikipedia
- Betamethasone_phosphate
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.9 mg/mL ALOGPS logP 1.21 ALOGPS logP 1.56 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 1.18 ChemAxon pKa (Strongest Basic) -3.4 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 141.36 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 113.37 m3·mol-1 ChemAxon Polarizability 45.43 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets

- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [PubMed:15634032]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Structural molecule activity
- Specific Function
- Plays important roles in the innate immune response as effector of glucocorticoid-mediated responses and regulator of the inflammatory process. Has anti-inflammatory activity (PubMed:8425544). Play...
- Gene Name
- ANXA1
- Uniprot ID
- P04083
- Uniprot Name
- Annexin A1
- Molecular Weight
- 38713.855 Da
References
- Serres M, Viac J, Comera C, Schmitt D: Expression of annexin I in freshly isolated human epidermal cells and in cultured keratinocytes. Arch Dermatol Res. 1994;286(5):268-72. [PubMed:8060156]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [PubMed:20482443]
- FDA Approved Drug Products: Celestone Soluspan (betamethasone sodium phosphate and betamethasone acetate) injectable suspension [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [PubMed:20482443]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Steroid binding
- Specific Function
- Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
- Gene Name
- SERPINA6
- Uniprot ID
- P08185
- Uniprot Name
- Corticosteroid-binding globulin
- Molecular Weight
- 45140.49 Da
References
- Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [PubMed:23300763]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [PubMed:15634032]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [PubMed:8786566]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, Swaan PW: Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharm Res. 2003 Nov;20(11):1794-803. [PubMed:14661924]
- Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [PubMed:24451000]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]
Drug created on September 03, 2018 17:11 / Updated on July 01, 2020 02:41