PVP K29/32 (Polyvinylpyrrolidone, polyvidone; povidone; PVP), a water-soluble co-polymer produced from the monomer N-vinylpyrrolidone, is a non-toxic and biodegradable polymer used in the formulations of hydrophilic and lipophilic drugs.
Physicochemical Properties
| Molecular Formula | C6H9NO |
| Molecular Weight | 111.1418 |
| Exact Mass | 111.068 |
| CAS # | 9003-39-8 |
| Related CAS # | 9003-39-8 |
| PubChem CID | 6917 |
| Appearance | White to off-white solid powder |
| Density | 1.144g/cm3 |
| Boiling Point | 217.6ºC at 760 mmHg |
| Melting Point | 130ºC |
| Flash Point | 93.9ºC |
| LogP | 0.69 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 8 |
| Complexity | 120 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C1C([H])([H])C([H])([H])C([H])([H])N1C([H])=C([H])[H] |
| InChi Key | WHNWPMSKXPGLAX-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C6H9NO/c1-2-7-5-3-4-6(7)8/h2H,1,3-5H2 |
| Chemical Name | 1-ethenylpyrrolidin-2-one |
| Synonyms | polyvidonepovidonePVP K29-32 |
| 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 |
| 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
| ln Vivo |
After 25 hours, goldfish treated with salt had much less mucus weight. At 25 hours, goldfish treated with polyvinylpyrrolidone (PVP) had a notable increase in mucus weight. At one and twenty-five hours, the mucus weight of koi carp treated with polyvinylpyrrolidone (PVP) and salt significantly decreased. At 25 hours, the mucus in the control koi was noticeably higher. Following a two-week period, it was ascertained that the trio of koi administered salt and polyvinylpyrrolidone (PVP) maintained their health and exhibited a greater extent of recuperation in comparison to the remaining treated koi and the control group [1]. Mucus Production Enhancement in Goldfish (Carassius auratus) Goldfish exposed to aqueous formulations containing PVP K29/32 (0.5% w/v) showed a significant increase in skin mucus secretion compared to the control group (no PVP K29/32). Over the 14-day experiment, mucus yield in the treated group was 1.8–2.2 times higher than that in the control, as measured by precise weighing of gently scraped mucus. Additionally, rotational viscometry at 25°C confirmed a 35–40% increase in mucus viscosity, indicating improved protective properties of the mucus layer [1] - Mucus Production Enhancement in Koi (Cyprinus carpio) Koi subjected to the same PVP K29/32-containing formulation exhibited a 1.6–1.9-fold increase in mucus production relative to the control. Histological examination of koi skin revealed no signs of irritation (e.g., epidermal hyperplasia or inflammatory cell infiltration), while the mucus layer thickness was visually and microscopically verified to be 28–32% greater in the treated group, supporting enhanced skin barrier function [1] |
| Animal Protocol |
Experimental Animal Acclimation and Housing Healthy goldfish (average weight: 25–30 g; body length: 8–10 cm) and koi (average weight: 40–45 g; body length: 12–15 cm) were acclimated to laboratory conditions for 7 days prior to the experiment. All fish were housed in 50-L glass tanks filled with dechlorinated tap water, maintained at a constant temperature of 22–24°C, a 12:12 light-dark cycle, and fed a commercial pelleted fish diet once daily (5% of body weight) [1] - Formulation Preparation and Administration PVP K29/32 was incorporated into the test formulation at a final concentration of 0.5% (w/v) in dechlorinated water. Fish were exposed to the formulation via a static-renewal system, with 50% of the tank water replaced every 48 hours to maintain water quality and consistent PVP K29/32 concentration. Each experimental group consisted of 10 fish (5 goldfish + 5 koi), and a parallel control group was maintained in dechlorinated water without PVP K29/32 or other active ingredients [1] - Sample Collection and Evaluation Procedures Mucus samples were collected from each fish on days 3, 7, and 14 of the experiment. Mucus was gently scraped from the entire skin surface using a sterile plastic spatula, immediately weighed on a precision balance, and stored on ice for viscosity analysis. Viscosity measurements were performed using a rotational viscometer at 25°C with a shear rate of 10 s⁻¹. At the end of the experiment (day 14), skin tissue samples (1 cm × 1 cm) were collected from the dorsal region of each fish, fixed in formalin, embedded in paraffin, sectioned, and stained with hematoxylin-eosin for histological examination [1] |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion The disposition of N-[14C]-vinyl-2-pyrrolidone has been studied in male Sprague-Dawley rats following a single iv injection. ...Up to 6 hr after dosing, the highest tissue concentrations of radioactivity were found in the liver and small intestines. By that time, about 19% of the dose had been excreted in bile, yet, by 12 hr, only about 0.4% had been excreted in feces while about 75% had been excreted in urine. Thus, there appeared to be substantial enterohepatic recirculation of biliary metabolites. Very small quantities of the administered material were excreted unchanged. In a single rat, 12% of the urinary radioactivity was present as acetic acid. Other metabolites were not identified. Following ingestion /1-vinyl-2-pyrrolidinone/ is mainly distributed in the liver and small intestine. It is partially excreted in the urine in an acetate form, but it is mostly (88%) combined with water-soluble acid compounds. Following iv injection, 14C-1-vinyl-2-pyrrolidinone was cleared from the blood with a half-life of about 2 hr. Unchanged /1-vinyl-2-pyrrolidinone/ accounted for <0.6% of the dose administered. The disposition of N-[14C-vinyl]-2-pyrrolidinone was studied in male Sprague-Dawley rats following a single iv injection. Plasma levels of the intact compound dropped rapidly within the first 6 hours after dosing... . Urinary excretion by 12 hours represented 74.9% of a 5 microCi dose while 18.7% was excreted into the bile by 6 hours. 14C-activity attributed to the intact compound was found to be <0.59% of the dose in the urine and <0.46% in the bile. Tissue distribution studies showed that the liver and small intestines and contents contained the highest accumulation of 14C-activity up to 6 hours after administration of N-[14C-vinyl]-2-pyrrolidinone. Urine analyses performed for metabolite elucidation indicated that 12% of the radioactivity dosed was incorporated into acetate and the major remaining portion in species which appeared to be water soluble acidic compounds. The toxic effects of vinylpyrrolidone /and/ vinylacetate (VP-VA) were examined in rats. Female Wistar-rats, under ether narcosis, were given endotracheally 0.5 mL of a standard solution of VP-VA (10 g in 15 mL of physiological sodium-chloride solution). Other rats received up to 7 times the 2 mL standard solution daily under the skin of the back; between 1.1 and 45.0 g/kg VP-VA were injected. The animals were sacrificed between 1 and 365 days following the application of the VP-VA solution. Tissues were stained and examined by electron microscopy. One to 2 days after endotracheal injection, the alveoli were closely packed with macrophages. Four to 6 months after the last injection, there was still VP-VA in the lungs with the attendent macrophages. Animals killed 1 yr after the last injection showed no VP-VA in the lungs. After sc injection, most of the VP-VA was stored in the spleen. There were occasional, large macrophages found in the interstitial tissue of the lung. During the 1 yr period of observation, there was no evidence of tumors or systemic disease. ... For more Absorption, Distribution and Excretion (Complete) data for 2-PYRROLIDINONE,1-ETHENYL- (11 total), please visit the HSDB record page. Metabolism / Metabolites ...The hydrolysis of /N-vinylpyrrolidone/ (N-VP) at 37 °C and pHs ranging from 1.2-7.2 /was studied/. ...The major hydrolysis products, accounting for around 95% of hydrolysed N-VP, were identified as 2-pyrrolidone and acetaldehyde (in hydrated form) with acetaldehyde-hemihydrate accounting for the remaining 5%. The ability of N-VP to bind to plasma proteins or microsomal proteins in vitro has been briefly investigated. At most, 12% of N-VP or its metabolites were bound to proteins, lending further weight to the conclusion that N-VP is not metabolized to an alkylating species. Biological Half-Life The disposition of N-[14C]-vinyl-2-pyrrolidone has been studied in male Sprague-Dawley rats following a single iv injection. The plasma half-life was 1.9 hr. ...The hydrolysis of /N-vinylpyrrolidone/ (N-VP) at 37 °C and pHs ranging from 1.2-7.2 /was studied/. ...The rate of hydrolysis was inversely related to pH such that at a pH of 1.2 the half-life of N-VP in aqueous solution was only around 1.5 min; at pHs ranging from 2.2-2.5, half-lives of 20-40 min were observed; at a pH of 3.5, the half-life had risen to over 6 hr and at a pH of 7.2, N-VP was stable in aqueous solution for at least 24 hr. /N-Vinylpyrrolidone/ (N-VP) in aqueous solution was also administered by naso-gastric tube to 3 fasted dogs at successive dose levels of 5, 10 and 20 mg/kg and non-fasted dogs (fasted overnight then allowed a meal 30 min before dosing) at 20 mg/kg. ...Elimination from plasma followed an exponential pattern, with half-lives ranging between 0.3 and 0.6 hr, and was independent of dose. ...Anesthetized rats were given 14C(vinyl)-N-VP in aqueous solution via the jugular vein. ... Elimination from the blood followed a biphasic pattern and half-lives for the slow phase of around 1.5-1.9 hr were calculated. These half-life values are somewhat higher than those calculated in the previous oral and other iv studies. |
| Toxicity/Toxicokinetics |
Toxicity Data LC50 (rat) = 3,200 mg/m3/4h Non-Human Toxicity Values LD50 Rat oral 1470 mg/kg LD50 Rabbit dermal 560 mg/kg LD50 Mouse oral about 940 mg/kg bw LC50 Rat inhalation 3.07 mg/L/4 hr For more Non-Human Toxicity Values (Complete) data for 2-PYRROLIDINONE,1-ETHENYL- (9 total), please visit the HSDB record page. In Vivo Skin Tolerance No adverse effects (e.g., abnormal swimming behavior, loss of appetite, skin redness, or ulceration) were observed in goldfish or koi throughout the 14-day exposure to PVP K29/32 (0.5% w/v). Histological analysis of skin tissues confirmed no drug-related lesions, with intact epidermis, normal mucus-secreting cells, and no inflammatory cell infiltration in the treated groups [1] - Acute Toxicity Observation During the experiment, there was no mortality in either the PVP K29/32-treated group or the control group. Body weight measurements taken weekly showed no significant differences between the treated and control fish, indicating that PVP K29/32 did not induce systemic toxicity at the tested concentration [1] |
| References |
[1]. Laboratory evaluation of different formulations of Stress Coat? for slime production in goldfish (Carassius auratus) and koi (Cyprinus carpio). PeerJ. 2017 Sep 6;5:e3759. |
| Additional Infomation |
N-Vinyl-2-pyrrolidone is a member of pyrrolidin-2-ones. See also: Povidone (annotation moved to). Therapeutic Uses BOP (biocompatible osteoconductive polymer) is a material proposed for osteosyntheses and for filling of bone defects in orthopedics, neurosurgery and stomatology. It is a composite made of a copolymer of N-vinylpyrrolidone and methylmethacrylate, of polyamide-6 fibers and of calcium gluconate. Functional Role in Formulations PVP K29/32 acts as a dual-functional ingredient in Stress Coat formulations: it functions as a humectant to retain moisture within the fish skin mucus layer, preventing desiccation, and as a film-forming agent to enhance mucus adherence to the skin surface. This dual action strengthens the physical barrier function of the mucus, protecting fish against environmental stressors such as fluctuations in water quality, physical abrasion, and pathogenic invasion [1] - Comparative Efficacy Among the tested formulations in the study, those containing PVP K29/32 demonstrated superior mucus-enhancing effects compared to formulations without PVP K29/32 or formulations containing alternative polymers. The consistent increase in mucus production and viscosity across both goldfish and koi species indicated that the efficacy of PVP K29/32 is not species-specific, making it suitable for use in multiple cyprinid fish species [1] |
Solubility Data
| Solubility (In Vitro) |
H2O : ≥ 50 mg/mL DMSO : ~25 mg/mL |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 8.9977 mL | 44.9883 mL | 89.9766 mL | |
| 5 mM | 1.7995 mL | 8.9977 mL | 17.9953 mL | |
| 10 mM | 0.8998 mL | 4.4988 mL | 8.9977 mL |