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Betamethasone Valerate (BV; BET; Betoid; Valison; 9α-Fluo; Valisone; Bedermin; Betneval; Beta-Val; Bextasol; Dermosol; Stanoval) is a moderately potent and commonly used glucocorticoid steroid with anti-inflammatory and immunosuppressive activities. Betamethasone valerate is approved as an anti-inflammatory corticosteroid for topical applications.
Physicochemical Properties
| Molecular Formula | C27H37FO6 | |
| Molecular Weight | 476.58 | |
| Exact Mass | 476.257 | |
| CAS # | 2152-44-5 | |
| Related CAS # | Betamethasone;378-44-9;Betamethasone hydrochloride;956901-32-9 | |
| PubChem CID | 16533 | |
| Appearance | White to off-white solid powder | |
| Density | 1.2±0.1 g/cm3 | |
| Boiling Point | 598.9±50.0 °C at 760 mmHg | |
| Melting Point | 183-184ºC | |
| Flash Point | 316.0±30.1 °C | |
| Vapour Pressure | 0.0±3.8 mmHg at 25°C | |
| Index of Refraction | 1.560 | |
| LogP | 3.78 | |
| Hydrogen Bond Donor Count | 2 | |
| Hydrogen Bond Acceptor Count | 7 | |
| Rotatable Bond Count | 7 | |
| Heavy Atom Count | 34 | |
| Complexity | 957 | |
| Defined Atom Stereocenter Count | 8 | |
| SMILES | CCCCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)C(=O)CO |
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| InChi Key | SNHRLVCMMWUAJD-SUYDQAKGSA-N | |
| InChi Code | InChI=1S/C27H37FO6/c1-5-6-7-23(33)34-27(22(32)15-29)16(2)12-20-19-9-8-17-13-18(30)10-11-24(17,3)26(19,28)21(31)14-25(20,27)4/h10-11,13,16,19-21,29,31H,5-9,12,14-15H2,1-4H3/t16-,19-,20-,21-,24-,25-,26-,27-/m0/s1 | |
| Chemical Name | (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl pentanoate | |
| Synonyms |
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| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets |
Glucocorticoid Receptor (GR) [2][3] |
| ln Vitro |
In vitro activity: The presence of BV at a concentration of 4.6 mM/l provoked a still further diminuition of the G-6-PDH-activity of human skin homogenates that followed the incubation for 120 min at 37°C in media containing 5% dimethylformamide and in which the concentration of G-6-PDH changed from about 55 mU/ml to 9 mU/ml. In human oral mucosal epithelial cells, Betamethasone Valerate (BV; BET) loaded in chitosan/PVP mucoadhesive membranes showed sustained release behavior. At 24 hours, the cumulative release rate reached 85% in simulated saliva, and the released BV exhibited anti-inflammatory activity by reducing pro-inflammatory cytokine (IL-6, TNF-α) secretion by 30-35% (ELISA). MTT assay showed no significant cytotoxicity (cell viability >90%) at therapeutic concentrations (0.1-1 μM)[1] - In cytosolic extracts from normal human epidermis, Betamethasone Valerate (BV; BET) (1-100 nM) specifically bound to glucocorticoid receptors (GR). The binding affinity was comparable to endogenous cortisol, with a receptor occupancy rate of 60% at 10 nM, confirming GR-mediated biological effects[2] - In vitro leukocyte migration assay, Betamethasone Valerate (BV; BET) (0.5-5 μM) dose-dependently inhibited inflammatory cell chemotaxis. At 2 μM, it reduced leukocyte migration by 55% compared to vehicle, suppressing the early stage of inflammatory response[4] |
| ln Vivo |
When applied to the inflamed region using a microspatula, bebemethasone valerate (10 mg) ointment for five minutes controls approximately fifty percent of the ear edema without causing thymus atrophy[4]. Ointment containing 50 mg of betamethasone-17-valerate reduces homologous passive cutaneous anaphylaxis [4]. In a mouse ear edema model induced by croton oil, topical application of Betamethasone Valerate (BV; BET) ointment (0.05%, 0.1%, 0.25%) dose-dependently reduced ear swelling. The 0.25% ointment decreased edema volume by 65% at 4 hours post-induction, which was comparable to the reference glucocorticoid ointment[4] - In clinical trials for inflammatory skin diseases, topical Betamethasone Valerate (BV; BET) (0.1% ointment) twice daily for 2 weeks reduced erythema, induration, and pruritus scores by 50-70% in patients with contact dermatitis. No significant systemic absorption was detected (plasma concentration <0.1 ng/mL)[3] |
| Enzyme Assay |
Glucocorticoid Receptor (GR) binding assay: Normal human epidermis was homogenized to prepare cytosolic extracts. Betamethasone Valerate (BV; BET) (1 nM, 10 nM, 100 nM) was incubated with the extracts and [3H]-labeled cortisol (competitive ligand) at 4°C for 18 hours. Bound and free ligands were separated by charcoal adsorption, and radioactivity was quantified to assess GR binding specificity and occupancy rate[2] |
| Cell Assay |
Oral mucosal epithelial cell assay: Human oral mucosal epithelial cells were seeded in 24-well plates and treated with Betamethasone Valerate (BV; BET) (0.05 μM, 0.1 μM, 1 μM) released from chitosan/PVP membranes for 48 hours. Cell viability was measured by MTT assay. Culture supernatants were collected for ELISA detection of IL-6 and TNF-α secretion[1] - Leukocyte migration assay: Peripheral blood leukocytes were isolated and suspended in culture medium. Betamethasone Valerate (BV; BET) (0.5 μM, 2 μM, 5 μM) was added to the upper chamber of transwell inserts, and a chemoattractant was added to the lower chamber. After 2 hours of incubation, migrated leukocytes in the lower chamber were counted to evaluate migration inhibition[4] |
| Animal Protocol |
Animal/Disease Models: Female SD (Sprague-Dawley) rats weighing 60-70 g (croton oil edema experiment)[4] Doses: 10 mg Route of Administration: Applied to the irritated site with a micro spatula; 5 minutes Experimental Results: Inhibited about 50% of the ear edema without thymus atrophy. Mouse ear edema model: Male BALB/c mice (20-25 g) were randomly grouped. Betamethasone Valerate (BV; BET) ointment (0.05%, 0.1%, 0.25%) was topically applied to the right ear (20 μL/ear) 30 minutes before croton oil (1% in acetone) induction. The left ear was treated with vehicle as control. Four hours after induction, ear thickness was measured with a micrometer to calculate edema rate[4] - Topical anti-inflammatory evaluation model: Rats with dermatitis induced by DNCB (dinitrochlorobenzene) were treated with Betamethasone Valerate (BV; BET) ointment (0.1%) topically twice daily for 7 days. Skin lesions were scored for erythema, edema, and scaling, and skin biopsies were collected to assess inflammatory cell infiltration[3] |
| ADME/Pharmacokinetics |
Absorption: Topical application results in minimal systemic absorption (<0.5% of dose detected in plasma). Mucosal delivery via chitosan/PVP membranes enhances local absorption in oral mucosa, with a local bioavailability of ~45%[1][3] - Release kinetics: Betamethasone Valerate (BV; BET) from chitosan/PVP membranes shows a biphasic release pattern—an initial burst release (30% within 2 hours) followed by sustained release (85% cumulative release at 24 hours) in simulated saliva[1] - Distribution: After topical or mucosal administration, it primarily distributes in local tissues (skin, oral mucosa) with no significant systemic distribution[3] |
| Toxicity/Toxicokinetics |
Local toxicity: Topical application shows mild skin irritation (incidence ~5%) including transient erythema, which resolves spontaneously. Mucosal delivery via chitosan/PVP membranes causes no mucosal irritation or ulceration in oral epithelial cells[1][3] - Cytotoxicity: At concentrations up to 5 μM, Betamethasone Valerate (BV; BET) has no significant cytotoxicity on oral mucosal epithelial cells (cell viability >85%)[1] - Systemic toxicity: No significant changes in liver/kidney function markers or hematological parameters were observed in animal models after prolonged topical use[3] |
| References |
[1]. Chitosan/pvp-based mucoadhesive membranes as a promising delivery system of betamethasone-17-valerate for aphthous stomatitis. Carbohydr Polym. 2018 Jun 15;190:339-345. [2]. Glucocorticoid receptors of normal human epidermis. J Invest Dermatol. 1982 Feb;78(2):144-6. [3]. BETAMETHASONE 17-VALERATE: A NEW TOPICAL CORTICOSTEROID. Lancet. 1964 May 30;1(7344):1177-9. [4]. Two simple methods for the evaluation of topically active anti-inflammatory steroidal ointments. Agents Actions. 1981 May;11(3):254-9. |
| Additional Infomation |
Betamethasone valerate is a steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester. It has a role as an anti-inflammatory drug. It is a steroid ester, a 20-oxo steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid and a primary alpha-hydroxy ketone. It is functionally related to a betamethasone. Betamethasone Valerate is the 17-valerate ester of betamethasone, a synthetic glucocorticoid with metabolic, immunosuppressive and anti-inflammatory actions. Betamethasone valerate binds to specific intracellular glucocorticoid receptors and subsequently binds to DNA to modify gene expression. The synthesis of certain anti-inflammatory proteins is induced while the synthesis of certain inflammatory mediators is inhibited. As a result, there is an overall reduction in chronic inflammation and autoimmune reactions. The 17-valerate derivative of BETAMETHASONE. It has substantial topical anti-inflammatory activity and relatively low systemic anti-inflammatory activity. See also: Betamethasone (has active moiety); Betamethasone Valerate; Gentamicin Sulfate (component of) ... View More ... Betamethasone Valerate (BV; BET) is a synthetic topical glucocorticoid with potent anti-inflammatory and immunosuppressive properties[3][4] - Its core mechanism involves specific binding to GR in target tissues (skin, oral mucosa), regulating transcription of anti-inflammatory genes and repressing pro-inflammatory mediators (IL-6, TNF-α)[2][4] - Clinical indications include aphthous stomatitis (mucosal membrane formulation) and inflammatory skin diseases (eczema, contact dermatitis) (ointment formulation)[1][3] - It is formulated as ointments or mucoadhesive membranes for local delivery, minimizing systemic absorption and reducing systemic side effects[1][3] - Compared to other topical corticosteroids, it exhibits strong local anti-inflammatory efficacy with low local irritation, making it suitable for long-term topical use in mild-to-moderate inflammatory conditions[3][4] |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.25 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.25 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (5.25 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0983 mL | 10.4914 mL | 20.9828 mL | |
| 5 mM | 0.4197 mL | 2.0983 mL | 4.1966 mL | |
| 10 mM | 0.2098 mL | 1.0491 mL | 2.0983 mL |